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Use of Carbon Dioxide in Polymer Synthesis

  • Annalisa Abdel AzimEmail author
  • Alessandro CordaraEmail author
  • Beatrice Battaglino
  • Angela Re
Chapter
Part of the Environmental Chemistry for a Sustainable World book series (ECSW, volume 41)

Abstract

The possibility of developing biotechnological processes based on emitted carbon dioxide (CO2) for obtaining diverse products offers an exciting and visionary path from an ecologically destructive and resource-exhausting societal and economical model to a resource-conserving and environmentally friendly one. Microorganisms-based CO2 sequestration is best positioned to represent a prominent alternative to conventional CO2 sequestration technologies consisting of CO2 capture, CO2 separation, and CO2 storage, which present shortfalls such as energy and operational costs and the production of degradation products injurious to human health and natural ecosystems. Without neglecting the bottlenecks inherent into bio-manufacturing, it is worth highlighting that, differently from microbial CO2 sequestration, microorganisms are not restricted to be used solely as desirable carbon sinks but also as catalysts that can simultaneously capture CO2 and produce value-added chemicals. Rather than being a niche market, the CO2-based biopolymers market is expected to witness significant growth.

Herein, we highlight the usage of CO2 as carbon substrate in the synthesis of polymers or polymer building blocks through biological processes. Together with the advances reached by synthetic biology and metabolic engineering capacities, a number of microorganisms have been engaged in the construction of CO2-based cell factories. The present chapter captures the main breakthroughs in the biotransformation of CO2 into different classes of valuable intermediates towards polymer synthesis.

Keywords

Carbon dioxide Metabolic engineering Enzymatic catalysis Aromatic and aliphatic monomer In vivo synthetic polymer Plastic Circular economy Bio-refinery Eco-design Recyclability 

Abbreviations

1,3-PDO

1,3-Propanediol

2,3-BDO

2,3-Butanediol

3-HP

3-Hydroxypropionic

3-HPA

3-Hydroxypropionaldehyde

3-HV

3-Hydroxyvalerate

4HB

4-Hydroxybutyrate

5-AVA

δ-Aminovaleric acid

6-ACA

ε-Aminocaproic acid

ADH

Alcohol dehydrogenase

ADMET

Acyclic diene metathesis

ATP

Adenosine triphosphate

ATRP

Atom transfer radical polymerization

C3H

p-Coumarate-3-hydroxylase

CA

Carbonic anhydrase

CAGR

Compound annual growth rate

CDW

Cell dry weight

CO

Carbon monoxide

CO2

Carbon dioxide

CP

Cyanophycin

CRISPRi

Clustered regularly interspaced short palindromic repeats interference

DAHPS

3-Deoxy-D-arabino-heptulosonate-7-phosphate synthase

DHAP

Dihydroxyacetone phosphate

DHCA

3,4-Dihydroxycinnamic acid

EPS

Extracellular polymeric substances

fbr-DAHPS

Feedback-inhibition-resistant 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase

GABA

γ-Aminobutyric acid

GDP

Guanosine diphosphate

GlyDH

Glycerol dehydrogenase

H2

Hydrogen

HCO3-

Hydrogen carbonate

IPTG

Isopropyl β-D-1-thiogalactopyranoside

KGD

Ketoglutarate decarboxylase

LDH

Lactate dehydrogenases

MCR

Malonyl-CoA reductase

MgCO3

Magnesium carbonate

MSA

Malonate semialdehyde

NADH

Nicotinamide adenine dinucleotide

NADPH

Nicotinamide adenine dinucleotide phosphate

NAGK

N-Acetyl-l-glutamate kinase

n-Bu4NBr-DMF

Tetra-n-butylammonium bromide-dimethylformamide

NMP

Nitroxide-mediated polymerization

Nox

Nitrogen oxides

O2

Oxygen

P(3HB-co-3HP)

Poly(3-hydroxybutyrate-co-3-hydroxypropionate) copolymer

P(3HB-co-4HB)

Poly(3-hydroxubutyrate-co-4-hydroxybutyrate) copolymer

P3HB

Poly-3-hydroxybutyrate

PAD

Phenolic acid decarboxylase

PBS

Polybutylene succinate

p-CA

p-Coumaric acid

PDC

p-Hydroxycinnamic acid decarboxylase

PEP

Phosphoenolpyruvate

PHAmcl

Medium-chain length polyhydroxyalkanoates

PHAs

Polyhydroxyalkanoates

PHAscl

Short-chain length polyhydroxyalkanoates

PHB

Poly(3-hydroxybutyrate)

p-HBA

p-Hydroxybenzene

p-HS

p-Hydroxystyrene

PHV

Polyhydroxyvalerate

PLA

Polylactic acid

PTT

Polytrimethylene terephthalate

PyDC

Pyruvate decarboxylase

rAcCoA

Oxygen-sensitive reductive acetyl-CoA pathway

RAFT

Reversible addition fragmentation chain-transfer polymerization

rPP cycle

Reductive pentose phosphate cycle

rTCA

Reductive tricarboxylic acid cycle

SPPS

Solid-phase peptide synthesis

SSD

Succinate-semialdehyde dehydrogenase

THF

Tetrahydrofuran

References

  1. Ahn JH, Jang YS, Lee SY (2016) Production of succinic acid by metabolically engineered microorganisms. Curr Opin Biotechnol 42:54–66.  https://doi.org/10.1016/j.copbio.2016.02.034CrossRefGoogle Scholar
  2. Allen MM, Hutchison F, Weathers PJ (1980) Cyanophycin granule polypeptide formation and degradation in the cyanobacterium Aphanocapsa 6308. J Bacteriol 141:687–693.  https://doi.org/10.1016/j.virol.2005.04.003CrossRefGoogle Scholar
  3. Andreeßen B, Steinbüchel A (2010) Biosynthesis and biodegradation of 3-hydroxypropionate-containing polyesters. Appl Environ Microbiol 76:4919–4925.  https://doi.org/10.1128/AEM.01015-10CrossRefGoogle Scholar
  4. Andreeßen B, Taylor N, Steinbüchela A (2014) Poly(3-hydroxypropionate): a promising alternative to fossil fuel-based materials. Appl Environ Microbiol 80:6574–6582.  https://doi.org/10.1128/AEM.02361-14CrossRefGoogle Scholar
  5. Angermayr SA, Hellingwerf KJ (2013) On the use of metabolic control analysis in the optimization of cyanobacterial biosolar cell factories. J Phys Chem B 117:11169–11175.  https://doi.org/10.1021/jp4013152CrossRefGoogle Scholar
  6. Angermayr SA, Paszota M, Hellingwerf KJ (2012) Engineering a cyanobacterial cell factory for production of lactic acid. Appl Environ Microbiol 78:7098–7106.  https://doi.org/10.1128/AEM.01587-12CrossRefGoogle Scholar
  7. Aresta M, Dibenedetto A (2002) Development of environmentally friendly syntheses: use of enzymes and biomimetic systems for the direct carboxylation of organic substrates. Rev Mol Biotechnol 90:113–128.  https://doi.org/10.1016/S1389-0352(01)00069-1CrossRefGoogle Scholar
  8. Aresta M, Dibenedetto A (2007) Utilisation of CO2 as a chemical feedstock: opportunities and challenges. J Chem Soc Dalton Trans:2975–2992.  https://doi.org/10.1039/b700658f
  9. Bauri K, Nandi M, De P (2018) Amino acid-derived stimuli-responsive polymers and their applications. Polym Chem 9:1257–1287.  https://doi.org/10.1039/c7py02014gCrossRefGoogle Scholar
  10. Bellini E, Ciocci M, Savio S, Antonaroli S, Seliktar D, Melino S, Congestri R (2018) Trichormus variabilis (cyanobacteria) biomass: from the Nutraceutical products to novel EPS-cell/protein carrier systems. Mar Drugs 16.  https://doi.org/10.3390/md16090298CrossRefGoogle Scholar
  11. Ben-Bassat A, Breinig S, Crum GA, Huang L, Altenbaugh ALB, Rizzo N, Trotman RJ, Vannelli T, Sariaslani FS, Haynie SL (2007) Preparation of 4-Vinylphenol using pHCA decarboxylase in a two-solvent medium. Org Process Res Dev 11(2):278–285.  https://doi.org/10.1021/OP0602472CrossRefGoogle Scholar
  12. Berg H, Ziegler K, Piotukh K, Baier K, Lockau W, Volkmer-engert R (2000) Biosynthesis of the cyanobacterial reserve polymer multi-L-arginyl-poly-L-aspartic acid (cyanophycin) mechanism of the cyanophycin synthetase reaction studied with synthetic primers. Eur J Biochem 5570:5561–5570.  https://doi.org/10.1046/j.1432-1327.2000.01622.xCrossRefGoogle Scholar
  13. Berg IA, Kockelkorn D, Buckel W, Fuchs G (2007) A 3-hydroxypropionate/4-hydroxybutyrate autotrophic carbon dioxide assimilation pathway in archaea. Science 318:1782–1786.  https://doi.org/10.1126/science.1149976CrossRefGoogle Scholar
  14. Buckel W (2001) Unusual enzymes involved in five pathways of glutamate fermentation. Appl Microbiol Biotechnol 57:263–273.  https://doi.org/10.1007/s002530100773CrossRefGoogle Scholar
  15. Cao W, Wang Y, Luo J, Yin J, Xing J, Wan Y (2018) Effectively converting carbon dioxide into succinic acid under mild pressure with Actinobacillus succinogenes by an integrated fermentation and membrane separation process. Bioresour Technol 266:26–33.  https://doi.org/10.1016/j.biortech.2018.06.016CrossRefGoogle Scholar
  16. Cespi D, Passarini F, Vassura I, Cavani F (2016) Butadiene from biomass, a life cycle perspective to address sustainability in the chemical industry. Green Chem 18:1625–1638.  https://doi.org/10.1039/c5gc02148kCrossRefGoogle Scholar
  17. Charubin K, Papoutsakis ET (2019) Direct cell-to-cell exchange of matter in a synthetic Clostridium syntrophy enables CO2 fixation, superior metabolite yields, and an expanded metabolic space. Metab Eng 52:9–19.  https://doi.org/10.1016/j.ymben.2018.10.006CrossRefGoogle Scholar
  18. Chee JY, Yoga SS, Lau NS, Ling SC, Abed RM, Sudesh K (2010) Bacterially produced polyhydroxyalkanoate (PHA): converting renewable resources into bioplastics. In: Current research, technology and education topics in applied microbiology and applied biotechnology. http://www.formatex.org/microbiology2/. (2014)
  19. Chen C, Wang Z, Li Z (2011) Thermoresponsive polypeptides from pegylated poly-l-glutamates. Biomacromolecules 12:2859–2863.  https://doi.org/10.1021/bm200849mCrossRefGoogle Scholar
  20. Chen H, Qiu T, Rong J et al (2015) Microalgal biofuel revisited: an informatics-based analysis of developments to date and future prospects. Appl Energy 155:585–598.  https://doi.org/10.1016/j.apenergy.2015.06.055CrossRefGoogle Scholar
  21. Chin JW, Anderson MA, Cui J, Spieker M (2014) Production of 1,3-propanediol in cyanobacteria (No. WO2014/062997 A1)Google Scholar
  22. Choi S, Song CW, Shin JH, Lee SY (2015a) Biorefineries for the production of top building block chemicals and their derivatives. Metab Eng 28:223–239.  https://doi.org/10.1016/j.ymben.2014.12.007CrossRefGoogle Scholar
  23. Choi WW, Yim SS, Lee HH, Kang JJ, Park JJ, Jeong JJ (2015b) Enhanced production of gamma-aminobutyrate (GABA) in recombinant Corynebacterium glutamicum by expressing glutamate decarboxylase active in expanded pH range. Microb Cell Factories 14:1–11.  https://doi.org/10.1186/s12934-015-0205-9CrossRefGoogle Scholar
  24. Chow YYS, Goh SJM, Su Z, Ng DHP, Lim CY, Lim NYN, Lin H, Fang L, Lee YK (2013) Continual production of glycerol from carbon dioxide by Dunaliella tertiolecta. Bioresour Technol 136:550–555.  https://doi.org/10.1016/j.biortech.2013.03.040CrossRefGoogle Scholar
  25. Claassens NJ, Sousa DZ, Dos Santos VAPM, De Vos WM, Van Der Oost J (2016) Harnessing the power of microbial autotrophy. Nat Rev Microbiol 14:692–706.  https://doi.org/10.1038/nrmicro.2016.130CrossRefGoogle Scholar
  26. Clomburg JM, Crumbley AM, Gonzalez R (2017) Industrial biomanufacturing: the future of chemical production. Science 355:aag0804.  https://doi.org/10.1126/SCIENCE.AAG0804CrossRefGoogle Scholar
  27. Debuissy T, Pollet E, Avérous L (2016) Synthesis of potentially biobased copolyesters based on adipic acid and butanediols: kinetic study between 1,4- and 2,3-butanediol and their influence on crystallization and thermal properties. Polymer 99:204–213.  https://doi.org/10.1016/j.polymer.2016.07.022CrossRefGoogle Scholar
  28. Debuissy T, Pollet E, Avérous L (2017) Enzymatic synthesis of biobased poly(1,4-butylene succinate-ran-2,3-butylene succinate) copolyesters and characterization. Influence of 1,4- and 2,3-butanediol contents. Eur Polym J 93:103–115.  https://doi.org/10.1016/j.eurpolymj.2017.04.045CrossRefGoogle Scholar
  29. Ding J, Shi F, Xiao C, Lin L, Chen L, He C, Zhuang X, Chen X (2011) One-step preparation of reduction-responsive poly(ethylene glycol)-poly(amino acid)s nanogels as efficient intracellular drug delivery platforms. Polym Chem 2:2857–2864.  https://doi.org/10.1039/c1py00360gCrossRefGoogle Scholar
  30. Doi Y, Segawa A, Kunioka M (1990) Biosynthesis and characterization of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in Alcaligenes eutrophus. Int J Biol Macromol 12:106–111.  https://doi.org/10.1016/0141-8130(90)90061-ECrossRefGoogle Scholar
  31. Duan H, Yamada Y, Sato S (2015) Efficient production of 1,3-butadiene in the catalytic dehydration of 2,3-butanediol. Appl Catal A Gen 491:163–169.  https://doi.org/10.1016/j.apcata.2014.12.006CrossRefGoogle Scholar
  32. Dudley QM, Nash CJ, Jewett MC (2019) Cell-free biosynthesis of limonene using enzyme-enriched Escherichia coli lysates. Synth Biol (Oxf) 4:ysz003.  https://doi.org/10.1093/synbio/ysz003CrossRefGoogle Scholar
  33. Durão J, Vale N, Gomes S, Gomes P, Barrias CC, Gales L (2018) Nitric oxide release from antimicrobial peptide hydrogels for wound healing. Biomol Ther 9:4.  https://doi.org/10.3390/biom9010004CrossRefGoogle Scholar
  34. Evans MC, Buchanan BB, Arnon DI (1966) A new ferredoxin-dependent carbon reduction cycle in a photosynthetic bacterium. Proc Natl Acad Sci 55:928–934.  https://doi.org/10.1073/pnas.55.4.928CrossRefGoogle Scholar
  35. Fu X, Shen Y, Fu W, Li Z (2013) Thermoresponsive Oligo(ethylene glycol) functionalized poly-L-cysteine. Macromolecules 38:1–32.  https://doi.org/10.1021/ma400678wCrossRefGoogle Scholar
  36. Garcia-Gonzalez L, Mozumder MSI, Dubreuil M, Volcke EIP, De Wever H (2015) Sustainable autotrophic production of polyhydroxybutyrate (PHB) from CO2 using a two-stage cultivation system. Catal Today 257:237–245.  https://doi.org/10.1016/j.cattod.2014.05.025CrossRefGoogle Scholar
  37. Gaspard J, Silas JA, Shantz DF, Jan JS (2010) Supramolecular assembly of lysine-b-glycine block copolypeptides at different solution conditions. Supramol Chem 22:178–185.  https://doi.org/10.1080/10610270903089746CrossRefGoogle Scholar
  38. Geyik AG, Kılıç B, Çeçen F (2016) Extracellular polymeric substances (EPS) and surface properties of activated sludges: effect of organic carbon sources. Environ Sci Pollut Res 23:1653–1663.  https://doi.org/10.1007/s11356-015-5347-0CrossRefGoogle Scholar
  39. Gontsarik M, Yaghmur A, Ren Q, Maniura-Weber K, Salentinig S (2019) From structure to function: pH-switchable antimicrobial Nano-self-assemblies. ACS Appl Mater Interfaces 11(3):2821–2829.  https://doi.org/10.1021/acsami.8b18618CrossRefGoogle Scholar
  40. Gordon GC, Korosh TC, Cameron JC, Markley AL, Begemann MB, Pfleger BF (2016) CRISPR interference as a titratable, trans-acting regulatory tool for metabolic engineering in the cyanobacterium Synechococcus sp. strain PCC 7002. Metab Eng 38:170–179.  https://doi.org/10.1016/j.ymben.2016.07.007CrossRefGoogle Scholar
  41. Haas R, Jin B, Zepf FT (2008) Production of poly(3-hydroxybutyrate) from waste potato starch. Biosci Biotechnol Biochem 72:253–256.  https://doi.org/10.1271/bbb.70503CrossRefGoogle Scholar
  42. Haba E, Vidal-Mas J, Bassas M, Espuny MJ, Llorens J, Manresa A (2007) Poly 3-(hydroxyalkanoates) produced from oily substrates by Pseudomonas aeruginosa 47T2 (NCBIM 40044): effect of nutrients and incubation temperature on polymer composition. Biochem Eng J 35:99–106.  https://doi.org/10.1016/J.BEJ.2006.11.021CrossRefGoogle Scholar
  43. Hamilton AC (2004) Medicinal plants, conservation and livelihoods. Biodivers Conserv 13:1477–1517.  https://doi.org/10.1023/B:BIOC.0000021333.23413.42CrossRefGoogle Scholar
  44. Han J, Hou J, Liu H, Cai S, Feng B, Zhou J, Xiang H (2010) Wide distribution among halophilic archaea of a novel polyhydroxyalkanoate synthase subtype with homology to bacterial type III synthases. Appl Environ Microbiol 76:7811–7819.  https://doi.org/10.1128/AEM.01117-10CrossRefGoogle Scholar
  45. Han D, Tong X, Zhao Y (2011) Fast photodegradable block copolymer micelles for burst release. Macromolecules 44:437–439.  https://doi.org/10.1021/ma102778dCrossRefGoogle Scholar
  46. Han PP, Sun Y, Wu XY, Yuan YJ, Dai YJ, Jia SR (2014) Emulsifying, flocculating, and physicochemical properties of exopolysaccharide produced by cyanobacterium Nostoc flagelliforme. Appl Biochem Biotechnol 172:36–49.  https://doi.org/10.1007/s12010-013-0505-7CrossRefGoogle Scholar
  47. Hanko EKR, Minton NP, Malys N (2017) Characterisation of a 3-hydroxypropionic acid-inducible system from Pseudomonas putida for orthogonal gene expression control in Escherichia coli and Cupriavidus necator. Sci Rep 7:1–13.  https://doi.org/10.1038/s41598-017-01850-wCrossRefGoogle Scholar
  48. Hasunuma T, Matsuda M, Kondo A (2016) Improved sugar-free succinate production by Synechocystis sp. PCC 6803 following identification of the limiting steps in glycogen catabolism. Metab Eng Commun 3:130–141.  https://doi.org/10.1016/j.meteno.2016.04.003CrossRefGoogle Scholar
  49. He M, Sun Y, Han B (2013) Green carbon science: scientific basis for integrating carbon resource processing, utilization, and recycling. Angew Chem Int Ed 52:9620–9633.  https://doi.org/10.1002/anie.201209384CrossRefGoogle Scholar
  50. Heinrich D, Raberg M, Steinbüchel A (2015) Synthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) from unrelated carbon sources in engineered Rhodospirillum rubrum. FEMS Microbiol Lett 362:1–9.  https://doi.org/10.1186/s12879-018-3021-0CrossRefGoogle Scholar
  51. Heinrich D, Raberg M, Fricke P, Kenny ST, Morales-Gamez L, Babu RP, O’connor KE, Steinbüchel A (2016) Synthesis gas (syngas)-derived medium-chain-length Polyhydroxyalkanoate synthesis in engineered Rhodospirillum rubrum. Appl Environ Microbiol 82(20):6132–6140.  https://doi.org/10.1128/AEM.01744-16CrossRefGoogle Scholar
  52. Herselman J, Bradfield MFA, Vijayan U, Nicol W (2017) The effect of carbon dioxide availability on succinic acid production with biofilms of Actinobacillus succinogenes. Biochem Eng J 117:218–228.  https://doi.org/10.1016/j.bej.2016.10.018CrossRefGoogle Scholar
  53. Herter S, Fuchs G, Bacher A, Eisenreich W (2002) A bicyclic autotrophic CO2fixation pathway in Chloroflexus aurantiacus. J Biol Chem 277:20277–20283.  https://doi.org/10.1074/jbc.M201030200CrossRefGoogle Scholar
  54. Higashi N, Sekine D, Koga T (2017) Temperature induced self-assembly of amino acid–derived vinyl block copolymers via dual phase transitions. J Colloid Interface Sci 500:341–348.  https://doi.org/10.1016/j.jcis.2017.04.027CrossRefGoogle Scholar
  55. Hirokawa Y, Maki Y, Tatsuke T, Hanai T (2016) Cyanobacterial production of 1,3-propanediol directly from carbon dioxide using a synthetic metabolic pathway. Metab Eng 34:97–103.  https://doi.org/10.1016/j.ymben.2015.12.008CrossRefGoogle Scholar
  56. Hirokawa Y, Goto R, Umetani Y, Hanai T (2017a) Construction of a novel D-lactate producing pathway from dihydroxyacetone phosphate of the Calvin cycle in cyanobacterium, Synechococcus elongatus PCC 7942. J Biosci Bioeng 124:54–61.  https://doi.org/10.1016/j.jbiosc.2017.02.016CrossRefGoogle Scholar
  57. Hirokawa Y, Matsuo S, Hamada H, Matsuda F, Hanai T (2017b) Metabolic engineering of Synechococcus elongatus PCC 7942 for improvement of 1,3-propanediol and glycerol production based on in silico simulation of metabolic flux distribution. Microb Cell Factories 16:1–12.  https://doi.org/10.1186/s12934-017-0824-4CrossRefGoogle Scholar
  58. Holowka EP, Deming TJ (2010) Synthesis and crosslinking of L-DOPA containing polypeptide vesicles. Macromol Biosci 10:496–502.  https://doi.org/10.1002/mabi.200900390CrossRefGoogle Scholar
  59. Huang Y, Tang Z, Zhang X, Yu H, Sun H, Pang X, Chen X (2013) PH-triggered charge-reversal polypeptide nanoparticles for cisplatin delivery: preparation and in vitro evaluation. Biomacromolecules 14:2023–2032.  https://doi.org/10.1021/bm400358zCrossRefGoogle Scholar
  60. Huber H, Gallenberger M, Jahn U, Eylert E, Berg IA, Kockelkorn D, Eisenreich W, Fuchs G (2008) A dicarboxylate/4-hydroxybutyrate autotrophic carbon assimilation cycle in the hyperthermophilic Archaeum Ignicoccus hospitalis. Proc Natl Acad Sci 105:7851–7856.  https://doi.org/10.1073/pnas.0801043105CrossRefGoogle Scholar
  61. Huo S, Wang Z, Zhu S, Zhou W, Dong R, Yuan Z (2012) Cultivation of Chlorella zofingiensis in bench-scale outdoor ponds by regulation of pH using dairy wastewater in winter, South China. Bioresour Technol 121:76–82.  https://doi.org/10.1016/j.biortech.2012.07.012CrossRefGoogle Scholar
  62. Iatrou H, Frielinghaus H, Hanski S, Ferderigos N, Ruokolainen J, Ikkala O, Richter D, Mays J, Hadjichristidis N (2007) Architecturally induced multiresponsive vesicles from well-defined polypeptides: formation of gene vehicles. Biomacromolecules 8:2173–2181.  https://doi.org/10.1021/bm070360fCrossRefGoogle Scholar
  63. Ito H (2001) Dissolution behavior of chemically amplified resist polymers lithography the aqueous base development step is one. IBM J Res Dev 45:683–695.  https://doi.org/10.1147/rd.455.0683CrossRefGoogle Scholar
  64. Jang YS, Kim B, Shin JH, Choi YJ, Choi S, Song CW, Lee J, Park HG, Lee SY (2012) Bio-based production of C2-C6 platform chemicals. Biotechnol Bioeng 109:2437–2459.  https://doi.org/10.1002/bit.24599CrossRefGoogle Scholar
  65. Jiang M, Ma J, Wu M, Liu R, Liang L, Xin F, Zhang W, Jia H, Dong W (2017) Progress of succinic acid production from renewable resources: metabolic and fermentative strategies. Bioresour Technol 245:1710–1717.  https://doi.org/10.1016/j.biortech.2017.05.209CrossRefGoogle Scholar
  66. Jones MD (2014) Catalytic transformation of ethanol into 1,3-butadiene. Chem Cent J 8:1–5.  https://doi.org/10.1186/s13065-014-0053-4CrossRefGoogle Scholar
  67. Jung DH, Choi W, Choi KY, Jung E, Yun H, Kazlauskas RJ, Kim BG (2013) Bioconversion of p-coumaric acid to p-hydroxystyrene using phenolic acid decarboxylase from B. amyloliquefaciens in biphasic reaction system. Appl Microbiol Biotechnol 97:1501–1511.  https://doi.org/10.1007/s00253-012-4358-8CrossRefGoogle Scholar
  68. Jung DH, Kim EJ, Jung E, Kazlauskas RJ, Choi KY, Kim BG (2016) Production of p-hydroxybenzoic acid from p-coumaric acid by Burkholderia glumae BGR1. Biotechnol Bioeng 113:1493–1503.  https://doi.org/10.1002/bit.25908CrossRefGoogle Scholar
  69. Kaneko T, Matsusaki M, Hang TT, Akashi M (2004) Thermotropic liquid-crystalline polymer derived from natural cinnamoyl biomonomers. Macromol Rapid Commun 25:673–677.  https://doi.org/10.1002/marc.200300143CrossRefGoogle Scholar
  70. Kaneko T, Thi TH, Shi DJ, Akashi M (2006) Environmentally degradable, high-performance thermoplastics from phenolic phytomonomers. Nat Mater 5:966–970.  https://doi.org/10.1038/nmat1778CrossRefGoogle Scholar
  71. Kanno M, Carroll AL, Atsumi S (2017) Global metabolic rewiring for improved CO2 fixation and chemical production in cyanobacteria. Nat Commun 8:1–11.  https://doi.org/10.1038/ncomms14724CrossRefGoogle Scholar
  72. Keller MW, Schut GJ, Lipscomb GL, Menon AL, Iwuchukwu IJ, Leuko TT, Thorgersen MP, Nixon WJ, Hawkins AS, Kelly RM, Adams MWW (2013) Exploiting microbial hyperthermophilicity to produce an industrial chemical, using hydrogen and carbon dioxide. Proc Natl Acad Sci 110:5840–5845.  https://doi.org/10.1073/pnas.1222607110CrossRefGoogle Scholar
  73. Kim BS (2000) Production of poly ( 3-hydroxybutyrate ) from inexpensive substrates. Enzym Microb Technol 27:774–777.  https://doi.org/10.1016/S0141-0229(00)00299-4CrossRefGoogle Scholar
  74. Kotharangannagari VK, Antoni S (2011) Photoresponsive reversible aggregation and dissolution of rod À coil polypeptide diblock copolymers. Macromolecules:4569–4573.  https://doi.org/10.1021/ma2008145CrossRefGoogle Scholar
  75. Kramer JR, Petitdemange R, Bataille L, Bathany K, Wirotius AL, Garbay B, Deming TJ, Garanger E, Lecommandoux S (2015) Quantitative side-chain modifications of methionine-containing elastin-like polypeptides as a versatile tool to tune their properties. ACS Macro Lett 4:1283–1286.  https://doi.org/10.1021/acsmacrolett.5b00651CrossRefGoogle Scholar
  76. Kruyer NS, Peralta-Yahya P (2017) Metabolic engineering strategies to bio-adipic acid production. Curr Opin Biotechnol 45:136–143.  https://doi.org/10.1016/j.copbio.2017.03.006CrossRefGoogle Scholar
  77. Kynadi AS, Suchithra TV (2014) Polyhydroxyalkanoates: biodegradable plastics for environmental conservation. In: Industrial & environmental biotechnology. Studium Press, pp 1–15.  https://doi.org/10.13140/RG.2.1.4642.5682
  78. Lan EI, Wei CT (2016) Metabolic engineering of cyanobacteria for the photosynthetic production of succinate. Metab Eng 38:483–493.  https://doi.org/10.1016/j.ymben.2016.10.014CrossRefGoogle Scholar
  79. Lan EI, Chuang DS, Shen CR, Lee AM, Ro SY, Liao JC (2015) Metabolic engineering of cyanobacteria for photosynthetic 3-hydroxypropionic acid production from CO2 using Synechococcus elongatus PCC 7942. Metab Eng 31:163–170.  https://doi.org/10.1016/j.ymben.2015.08.002CrossRefGoogle Scholar
  80. Le Yu J, Xia XX, Zhong JJ, Qian ZG (2014) Direct biosynthesis of adipic acid from a synthetic pathway in recombinant escherichia coli. Biotechnol Bioeng 111:2580–2586.  https://doi.org/10.1002/bit.25293CrossRefGoogle Scholar
  81. Le Yu J, Qian ZG, Zhong JJ (2018) Advances in bio-based production of dicarboxylic acids longer than C4. Eng Life Sci 18:668–681.  https://doi.org/10.1002/elsc.201800023CrossRefGoogle Scholar
  82. Lee KY, Mooney DJ (2012) Alginate: properties and biomedical applications. Prog Polym Sci (Oxf) 37:106–126.  https://doi.org/10.1016/j.progpolymsci.2011.06.003CrossRefGoogle Scholar
  83. Lee J, Sim SJ, Bott M, Um Y, Oh MK, Woo HM (2014) Succinate production from CO2-grown microalgal biomass as carbon source using engineered Corynebacterium glutamicum through consolidated bioprocessing. Sci Rep 4:1–6.  https://doi.org/10.1038/srep05819CrossRefGoogle Scholar
  84. Leite JP, Mota R, Durão J, Neves SC, Barrias CC, Tamagnini P, Gales L (2017) Cyanobacterium-derived extracellular carbohydrate polymer for the controlled delivery of functional proteins. Macromol Biosci 17:1–8.  https://doi.org/10.1002/mabi.201600206CrossRefGoogle Scholar
  85. Li J, Zheng XY, Fang XJ, Liu SW, Chen KQ, Jiang M, Wei P, Ouyang PK (2011) A complete industrial system for economical succinic acid production by Actinobacillus succinogenes. Bioresour Technol 102:6147–6152.  https://doi.org/10.1016/j.biortech.2011.02.093CrossRefGoogle Scholar
  86. Li C, Tao F, Ni J, Wang Y, Yao F, Xu P (2015) Enhancing the light-driven production of d-lactate by engineering cyanobacterium using a combinational strategy. Sci Rep 5:1–11.  https://doi.org/10.1038/srep09777CrossRefGoogle Scholar
  87. Lindsey AS, Jeskey H (1957) The Kolbe-Schmitt reaction. Chem Rev 57:583–620.  https://doi.org/10.1021/cr50016a001CrossRefGoogle Scholar
  88. Liu G, Dong CM (2012) Photoresponsive poly(S-(o-nitrobenzyl)-l-cysteine)-b-PEO from a l-cysteine N-carboxyanhydride monomer: synthesis, self-assembly, and phototriggered drug release. Biomacromolecules 13:1573–1583.  https://doi.org/10.1021/bm300304tCrossRefGoogle Scholar
  89. Liu J, Zhang X, Zhou S, Tao P, Liu J (2007) Purification and characterization of a 4-Hydroxybenzoate decarboxylase from chlamydophila pneumoniae AR39. Curr Microbiol 54:102–107.  https://doi.org/10.1007/s00284-006-0153-zCrossRefGoogle Scholar
  90. Liu G, Zhou L, Guan Y, Su Y, Dong CM (2014) Multi-responsive polypeptidosome: characterization, morphology transformation, and triggered drug delivery. Macromol Rapid Commun 35:1673–1678.  https://doi.org/10.1002/marc.201400343CrossRefGoogle Scholar
  91. Liu X, He J, Niu Y, Li Y, Hu D, Xia X, Lu Y, Xu W (2015) Photo-responsive amphiphilic poly(α-hydroxy acids) with pendent o-nitrobenzyl ester constructed via copper-catalyzed azide-alkyne cycloaddition reaction. Polym Adv Technol 26:449–456.  https://doi.org/10.1002/pat.3472CrossRefGoogle Scholar
  92. Lokitz BS, Convertine AJ, Ezell RG, Heidenreich A, Li Y, McCormick CL (2006) Responsive Nanoassemblies via Interpolyelectrolyte Complexation of Amphiphilic block copolymer micelles. Macromolecules 39:8594–8602.  https://doi.org/10.1021/MA061672YCrossRefGoogle Scholar
  93. Loscher R, Heide L (1994) Biosynthesis of p-Hydroxybenzoate from p-Coumarate and p-Coumaroyl-coenzyme a in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 106:271–279.  https://doi.org/10.1104/PP.106.1.271CrossRefGoogle Scholar
  94. Luo C, Zhao B, Li Z (2012) Dual stimuli-responsive polymers derived from α-amino acids: effects of molecular structure, molecular weight and end-group. Polymer 53:1725–1732.  https://doi.org/10.1016/j.polymer.2012.02.032CrossRefGoogle Scholar
  95. Lütte S, Pohlmann A, Zaychikov E, Schwartz E, Becher JR, Heumann H, Friedrich B (2012) Autotrophic production of stable-isotope-labeled arginine in Ralstonia eutropha strain H16. Appl Environ Microbiol 78:7884–7890.  https://doi.org/10.1128/AEM.01972-12CrossRefGoogle Scholar
  96. Ma Y, Fu X, Shen Y, Fu W, Li Z (2014) Irreversible low critical solution temperature Behaviors of thermal-responsive OEGylated poly( l -cysteine) containing Disulfide bonds. Macromolecules 47:4684–4689.  https://doi.org/10.1021/ma501104sCrossRefGoogle Scholar
  97. Mac DN, Fennell PS, Shah N, Maitland GC (2017) The role of CO2 capture and utilization in mitigating climate change. Nat Clim Chang 7:243–249.  https://doi.org/10.1038/nclimate3231CrossRefGoogle Scholar
  98. Mackiewicz M, Romanski J, Drozd E, Gruber-Bzura B, Fiedor P, Stojek Z, Karbarz M (2017) Nanohydrogel with N,N′-bis(acryloyl)cystine crosslinker for high drug loading. Int J Pharm 523:336–342.  https://doi.org/10.1016/j.ijpharm.2017.03.031CrossRefGoogle Scholar
  99. Maeda H, Dudareva N (2012) The Shikimate pathway and aromatic amino acid biosynthesis in plants. Annu Rev Plant Biol 63:73–105.  https://doi.org/10.1146/annurev-arplant-042811-105439CrossRefGoogle Scholar
  100. Maheswaran M, Ziegler K, Lockau W, Hagemann M, Forchhammer K (2006) PII-regulated arginine synthesis controls accumulation of cyanophycin in Synechocystis sp. strain PCC 6803. J Bacteriol 188:2730–2734.  https://doi.org/10.1128/JB.188.7.2730-2734.2006CrossRefGoogle Scholar
  101. Maji T, Banerjee S, Biswas Y, Mandal TK (2015) Dual-stimuli-responsive l -serine-based Zwitterionic UCST-type polymer with Tunable Thermosensitivity. Macromolecules 48:4957–4966.  https://doi.org/10.1021/acs.macromol.5b01099CrossRefGoogle Scholar
  102. Matsui T, Yoshida T, Hayashi T, Nagasawa T (2006) Purification, characterization, and gene cloning of 4-hydroxybenzoate decarboxylase of Enterobacter cloacae P240. Arch Microbiol 186:21–29.  https://doi.org/10.1007/s00203-006-0117-5CrossRefGoogle Scholar
  103. Matsusaki M, Kishida A, Stainton N, Ansell CWG, Akashi M (2001) Synthesis and characterization of novel biodegradable polymers composed of hydroxycinnamic acid and D,L-lactic acid. J Appl Polym Sci 82:2357–2364.  https://doi.org/10.1002/app.2085CrossRefGoogle Scholar
  104. Matthessen R, Fransaer J, Binnemans K, De Vos DE (2014) Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids. Beilstein J Org Chem 10:2484–2500.  https://doi.org/10.3762/bjoc.10.260CrossRefGoogle Scholar
  105. Mavrogiorgis D, Bilalis P, Karatzas A, Skoulas D, Fotinogiannopoulou G, Iatrou H (2014) Controlled polymerization of histidine and synthesis of well-defined stimuli responsive polymers. Elucidation of the structure-aggregation relationship of this highly multifunctional material. Polym Chem 5:6256–6278.  https://doi.org/10.1039/c4py00687aCrossRefGoogle Scholar
  106. McEwen JT, Kanno M, Atsumi S (2016) 2,3 Butanediol production in an obligate photoautotrophic cyanobacterium in dark conditions via diverse sugar consumption. Metab Eng 36:28–36.  https://doi.org/10.1016/j.ymben.2016.03.004CrossRefGoogle Scholar
  107. McKinlay JB, Vieille C, Zeikus JG (2007) Prospects for a bio-based succinate industry. Appl Microbiol Biotechnol 76:727–740.  https://doi.org/10.1007/s00253-007-1057-yCrossRefGoogle Scholar
  108. Miyasaka H, Okuhata H, Tanaka S, Onizuka T, Akiyam H (2013) Polyhydroxyalkanoate (PHA) production from carbon dioxide by recombinant cyanobacteria. Environ Biotechnol New Appr Prospect Appl.  https://doi.org/10.5772/54705Google Scholar
  109. Moon HJ, Ko DY, Park MH, Joo MK, Jeong B (2012) Temperature-responsive compounds as in situ gelling biomedical materials. Chem Soc Rev 41:4860–4883.  https://doi.org/10.1039/c2cs35078eCrossRefGoogle Scholar
  110. Mori H, Iwaya H, Nagai A, Endo T (2005) Controlled synthesis of thermoresponsive polymers derived from L-proline via RAFT polymerization. Chem Commun 38:4872–4874.  https://doi.org/10.1039/b509212dCrossRefGoogle Scholar
  111. Mori H, Kato I, Endo T (2009) Dual-stimuli-responsive block copolymers derived from proline derivatives. Macromolecules 42:4985–4992.  https://doi.org/10.1021/ma900706sCrossRefGoogle Scholar
  112. Ni J, Tao F, Wang Y, Yao F, Xu P (2016) A photoautotrophic platform for the sustainable production of valuable plant natural products from CO2. Green Chem 18:3537–3548.  https://doi.org/10.1039/c6gc00317fCrossRefGoogle Scholar
  113. Niederholtmeyer H, Wolfstädter BT, Savage DF, Silver PA, Way JC (2010) Engineering cyanobacteria to synthesize and export hydrophilic products. Appl Environ Microbiol 76:3462–3466.  https://doi.org/10.1128/AEM.00202-10CrossRefGoogle Scholar
  114. Noda S, Kondo A (2017) Recent advances in microbial production of aromatic chemicals and derivatives. Trends Biotechnol 35:785–796.  https://doi.org/10.1016/j.tibtech.2017.05.006CrossRefGoogle Scholar
  115. Nouha K, Kumar RS, Balasubramanian S, Tyagi RD (2018) Critical review of EPS production, synthesis and composition for sludge flocculation. J Environ Sci (China) 66:225–245.  https://doi.org/10.1016/j.jes.2017.05.020CrossRefGoogle Scholar
  116. Nozzi NE, Case AE, Carroll AL, Atsumi S (2017) Systematic approaches to efficiently produce 2,3-Butanediol in a marine Cyanobacterium. ACS Synth Biol 6:2136–2144.  https://doi.org/10.1021/acssynbio.7b00157CrossRefGoogle Scholar
  117. Ohkawa K, Shoumura K, Yamada M, Nishida A, Shirai H, Yamamoto H (2001) Photoresponsive peptide and polypeptide systems, 14. Biodegradation of Photocrosslinkable Copolypeptide hydrogels containing L-ornithine and δ-7-Coumaryloxyacetyl-L-ornithine residues. Macromol Biosci 1:149–156.  https://doi.org/10.1002/1616-5195(20010601)1:4<149::AID-MABI149>3.0.CO;2-OCrossRefGoogle Scholar
  118. Oliver JWK, Machado IMP, Yoneda H, Atsumi S (2013) Cyanobacterial conversion of carbon dioxide to 2,3-butanediol. Proc Natl Acad Sci 110:1249–1254.  https://doi.org/10.1073/pnas.1213024110CrossRefGoogle Scholar
  119. Pan Z, Lee W, Slutsky L, Clark RAF, Pernodet N, Rafailovich MH (2009) Adverse effects of titanium dioxide nanoparticles on human dermal fibroblasts and how to protect cells. Small 5:511–520.  https://doi.org/10.1002/smll.200800798CrossRefGoogle Scholar
  120. Pereira SB, Mota R, Vieira CP, Vieira J, Tamagnini P (2015) Phylum-wide analysis of genes/proteins related to the last steps of assembly and export of extracellular polymeric substances (EPS) in cyanobacteria. Sci Rep 5:1–16.  https://doi.org/10.1038/srep14835CrossRefGoogle Scholar
  121. Petitdemange R, Garanger E, Bataille L, Dieryck W, Bathany K, Garbay B, Deming TJ, Lecommandoux S (2017) Selective tuning of elastin-like polypeptide properties via methionine oxidation. Biomacromolecules 18:544–550.  https://doi.org/10.1021/acs.biomac.6b01696CrossRefGoogle Scholar
  122. Pfaff C, Gruber J, Glindemann N, Frentzen M, Sadre R (2013) Chorismate pyruvate-Lyase and 4-Hydroxy-3-solanesylbenzoate decarboxylase are required for Plastoquinone biosynthesis in the Cyanobacterium Synechocystis sp. PCC6803. J Biol Chem 289:2675–2686.  https://doi.org/10.1074/jbc.m113.511709CrossRefGoogle Scholar
  123. Qi C, Jiang H (2015) CO2 chemistry in SCUT Group: new methods for conversion of carbon dioxide into organic compounds. In: Advances in CO2 capture, sequestration, and conversion. American Chemical Society, Washington, DC, pp 71–108.  https://doi.org/10.1021/bk-2015-1194.ch003CrossRefGoogle Scholar
  124. Rabaey K, Rozendal RA (2010) Microbial electrosynthesis – revisiting the electrical route for microbial production. Nat Rev Microbiol 8:706–716.  https://doi.org/10.1038/nrmicro2422CrossRefGoogle Scholar
  125. Ragsdale SW, Pierce E (2008) Acetogenesis and the wood-Ljungdahl pathway of CO2 fixation. Biochim Biophys Acta Proteins Proteomics 1784:1873–1898.  https://doi.org/10.1016/j.bbapap.2008.08.012CrossRefGoogle Scholar
  126. Raza ZA, Abid S, Banat IM (2018) Polyhydroxyalkanoates: characteristics, production, recent developments and applications. Int Biodeterior Biodegrad 126:45–56.  https://doi.org/10.1016/j.ibiod.2017.10.001CrossRefGoogle Scholar
  127. Richter N, Zienert A, Hummel W (2011) A single-point mutation enables lactate dehydrogenase from Bacillus subtilis to utilize NAD+ and NADP+ as cofactor. Eng Life Sci 11:26–36.  https://doi.org/10.1002/elsc.201000151CrossRefGoogle Scholar
  128. Sadre R, Pfaff C, Buchkremer S (2012) Plastoquinone-9 biosynthesis in cyanobacteria differs from that in plants and involves a novel 4-hydroxybenzoate solanesyltransferase. Biochem J 442:621–629.  https://doi.org/10.1042/BJ20111796CrossRefGoogle Scholar
  129. Saha B, Bauri K, Bag A, Ghorai PK, De P (2016) Conventional fluorophore-free dual pH- and thermo-responsive luminescent alternating copolymer. Polym Chem 7:6895–6900.  https://doi.org/10.1039/c6py01738jCrossRefGoogle Scholar
  130. Sakimoto KK, Wong AB, Yang P (2016) Self-photosensitization of nonphotosynthetic bacteria for solar-to-chemical production. Science 351:74–77.  https://doi.org/10.1126/SCIENCE.AAD3317CrossRefGoogle Scholar
  131. Savakis P, Tan X, Du W, Branco Dos Santos F, Lu X, Hellingwerf KJ (2015) Photosynthetic production of glycerol by a recombinant cyanobacterium. J Biotechnol 195:46–51.  https://doi.org/10.1016/j.jbiotec.2014.12.015CrossRefGoogle Scholar
  132. Saxena S, Jayakannan M (2016) Enzyme and pH dual responsive l-amino acid based biodegradable polymer nanocarrier for multidrug delivery to cancer cells. J Polym Sci A Polym Chem 54:3279–3293.  https://doi.org/10.1002/pola.28216CrossRefGoogle Scholar
  133. Saxena S, Jayakannan M (2017) π-Conjugate fluorophore-tagged and enzyme-responsive l -amino acid polymer nanocarrier and their color-tunable intracellular FRET probe in cancer cells. Biomacromolecules 18:2594–2609.  https://doi.org/10.1021/acs.biomac.7b00710CrossRefGoogle Scholar
  134. Sepantafar M, Maheronnaghsh R, Mohammadi H, Radmanesh F, Hasani-sadrabadi MM, Ebrahimi M, Baharvand H (2017) Engineered hydrogels in Cancer therapy and diagnosis. Trends Biotechnol 35:1074–1087.  https://doi.org/10.1016/j.tibtech.2017.06.015CrossRefGoogle Scholar
  135. Shih PM, Zarzycki J, Niyogi KK, Kerfeld CA (2014) Introduction of a synthetic CO2-fixing photorespiratory bypass into a cyanobacterium. J Biol Chem 289:9493–9500.  https://doi.org/10.1074/jbc.C113.543132CrossRefGoogle Scholar
  136. Shin JH, Park SH, Oh YH, Choi JW, Lee MH, Cho JS, Jeong KJ, Joo JC, Yu J, Park SJ, Lee SY (2016) Metabolic engineering of Corynebacterium glutamicum for enhanced production of 5-aminovaleric acid. Microb Cell Factories 15:1–13.  https://doi.org/10.1186/s12934-016-0566-8CrossRefGoogle Scholar
  137. Simon RD (1971) Cyanophycin granules from the blue-green alga Anabaena cylindrica: a reserve material consisting of copolymers of aspartic acid and arginine. Proc Natl Acad Sci 68:265–267.  https://doi.org/10.1073/pnas.68.2.265CrossRefGoogle Scholar
  138. Simon RD (1976) The biosynthesis of multi-l-arginyl-poly(l-aspartic acid) in the filamentous cyanobacterium Anabaena cylindrica. BBA Enzymol 422:407–418.  https://doi.org/10.1016/0005-2744(76)90151-0CrossRefGoogle Scholar
  139. Straathof AJJ (2011) The proportion of downstream costs in fermentative production processes. Elsevier B.V.  https://doi.org/10.1016/B978-0-08-088504-9.00492-XCrossRefGoogle Scholar
  140. Sun J, Huang Y, Shi Q, Chen X, Jing X (2009) Oxygen carrier based on hemoglobin poly(L-lysine)-block-poly(L- phenylalanine) vesicles. Langmuir 25:13726–13729.  https://doi.org/10.1021/la901194kCrossRefGoogle Scholar
  141. Sun ZZ, Yeung E, Hayes CA, Noireaux V, Murray RM (2014) Linear DNA for rapid prototyping of synthetic biological circuits in an Escherichia coli based TX-TL cell-free system. ACS Synth Biol 3:387–397.  https://doi.org/10.1021/sb400131aCrossRefGoogle Scholar
  142. Syafiq IM, Huong KH, Shantini K, Vigneswari S, Aziz NA, Amirul AAA, Bhubalan K (2017) Synthesis of high 4-hydroxybutyrate copolymer by Cupriavidus sp. transformants using one-stage cultivation and mixed precursor substrates strategy. Enzym Microb Technol 98:1–8.  https://doi.org/10.1016/j.enzmictec.2016.11.011CrossRefGoogle Scholar
  143. Tamborini L, Fernandes P, Paradisi F, Molinari F (2018) Flow bioreactors as complementary tools for biocatalytic process intensification. Trends Biotechnol 36:73–88.  https://doi.org/10.1016/j.tibtech.2017.09.005CrossRefGoogle Scholar
  144. Tanaka K, Miyawaki K, Yamaguchi A, Khosravi-Darani K, Matsusaki H (2011) Cell growth and P(3HB) accumulation from CO2of a carbon monoxide-tolerant hydrogen-oxidizing bacterium, Ideonella sp. O-1. Appl Microbiol Biotechnol 92:1161–1169.  https://doi.org/10.1007/s00253-011-3420-2CrossRefGoogle Scholar
  145. Tenhaken R, Voglas E, Cock JM, Neu V, Huber CG (2011) Characterization of GDP-mannose dehydrogenase from the brown alga Ectocarpus siliculosus providing the precursor for the alginate polymer. J Biol Chem 286:16707–16715.  https://doi.org/10.1074/jbc.M111.230979CrossRefGoogle Scholar
  146. Thambi T, Yoon HY, Kim K, Kwon IC, Yoo CK, Park JH (2011) Bioreducible block copolymers based on poly(ethylene glycol) and poly(γ-Benzyl L-Glutamate) for intracellular delivery of camptothecin. Bioconjug Chem 22:1924–1931.  https://doi.org/10.1021/bc2000963CrossRefGoogle Scholar
  147. Thi TH, Matsusaki M, Shi D, Kaneko T, Akashi M (2008) Synthesis and properties of coumaric acid derivative homo-polymers. J Biomater Sci Polym Ed 19:75–85.  https://doi.org/10.1163/156856208783227668CrossRefGoogle Scholar
  148. Tong X, El-Zahab B, Zhao X, Liu Y, Wang P (2011) Enzymatic synthesis of L-lactic acid from carbon dioxide and ethanol with an inherent cofactor regeneration cycle. Biotechnol Bioeng 108:465–469.  https://doi.org/10.1002/bit.22938CrossRefGoogle Scholar
  149. Trautmann A, Watzer B, Wilde A, Forchhammer K, Posten C (2016) Effect of phosphate availability on cyanophycin accumulation in Synechocystis sp. PCC 6803 and the production strain BW86. Algal Res 20:189–196.  https://doi.org/10.1016/J.ALGAL.2016.10.009CrossRefGoogle Scholar
  150. Turk SCHJ, Kloosterman WP, Ninaber DK, Kolen KPAM, Knutova J, Suir E, Schürmann M, Raemakers-Franken PC, Müller M, De Wildeman SMA, Raamsdonk LM, Van Der Pol R, Wu L, Temudo MF, Van Der Hoeven RAM, Akeroyd M, Van Der Stoel RE, Noorman HJ, Bovenberg RAL, Trefzer AC (2016) Metabolic engineering toward sustainable production of Nylon-6. ACS Synth Biol 5:65–73.  https://doi.org/10.1021/acssynbio.5b00129CrossRefGoogle Scholar
  151. Varman AM, Yu Y, You L, Tang YJ (2013) Photoautotrophic production of D-lactic acid in an engineered cyanobacterium. Microb Cell Factories 12:1–8.  https://doi.org/10.1186/1475-2859-12-117CrossRefGoogle Scholar
  152. Vigneswari S, Vijaya S, Majid MIA, Sudesh K, Sipaut CS, Azizan MNM, Amirul AA (2009) Enhanced production of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) copolymer with manipulated variables and its properties. J Ind Microbiol Biotechnol 36:547–556.  https://doi.org/10.1007/s10295-009-0525-zCrossRefGoogle Scholar
  153. Vogel W, Heitz W (1990) With Phenethyl Side Chains 838:829–838.  https://doi.org/10.1002/macp.1990.021910411CrossRefGoogle Scholar
  154. Vogie KM, Mantick NA, Carlson GP (2004) Metabolism and toxicity of the styrene metabolite 4-Vinylphenol in CYP2E1 knockout mice. J Toxic Environ Health A 67:145–152.  https://doi.org/10.1080/15287390490264785CrossRefGoogle Scholar
  155. Volova TG, Kalacheva GS, Altukhova OV (2002) Autotrophic synthesis of polyhydroxyalkanoates by the bacteria Ralstonia eutropha in the presence of carbon monoxide. Appl Microbiol Biotechnol 58:675–678.  https://doi.org/10.1007/s00253-002-0941-8CrossRefGoogle Scholar
  156. Volova TG, Kiselev EG, Shishatskaya EI, Zhila NO, Boyandin AN, Syrvacheva DA, Vinogradova ON, Kalacheva GS, Vasiliev AD, Peterson IV (2013) Cell growth and accumulation of polyhydroxyalkanoates from CO2 and H2 of a hydrogen-oxidizing bacterium, Cupriavidus eutrophus B-10646. Bioresour Technol 146:215–222.  https://doi.org/10.1016/j.biortech.2013.07.070CrossRefGoogle Scholar
  157. Volova TG, Vinogradova ON, Zhila NO, Peterson IV, Kiselev EG, Vasiliev AD, Sukovatiy AG, Shishatskaya EI (2016) Properties of a novel quaterpolymer P(3HB/4HB/3HV/3HHx). Polymer 101:67–74.  https://doi.org/10.1016/j.polymer.2016.08.048CrossRefGoogle Scholar
  158. Volova TG, Vinogradova ON, Zhila NO, Kiselev EG, Peterson IV, Vasil’ev AD, Sukovatyi AG, Shishatskaya EI (2017) Physicochemical properties of multicomponent polyhydroxyalkanoates: novel aspects. Polym Sci Ser A 59:98–106.  https://doi.org/10.1134/S0965545X17010163CrossRefGoogle Scholar
  159. Wang D, Li Q, Li W, Liu Q, Xing J, Su Z (2008) Overexpression of a cyanobacterial carbonic anhydrase in Escherichia coli enhances succinic acid production. J Biotechnol 136:S26–S27.  https://doi.org/10.1016/j.jbiotec.2008.07.048CrossRefGoogle Scholar
  160. Wang Q, Ingram LO, Shanmugam KT (2011) Evolution of D-lactate dehydrogenase activity from glycerol dehydrogenase and its utility for D-lactate production from lignocellulose. Proc Natl Acad Sci U S A 108:18920–18925.  https://doi.org/10.1073/pnas.1111085108CrossRefGoogle Scholar
  161. Wang Y, Tao F, Ni J, Liab C, and Xu P (2015). Production of C3 platform chemicals from CO2 by genetically engineered cyanobacteria. Green Chem., 17:3100-3110.  https://doi.org/10.1039/C5GC00129CCrossRefGoogle Scholar
  162. Wang Y, Sun T, Gao X, Shi M, Wu L, Chen L, Zhang W (2016) Biosynthesis of platform chemical 3-hydroxypropionic acid (3-HP) directly from CO2in cyanobacterium Synechocystis sp. PCC 6803. Metab Eng 34:60–70.  https://doi.org/10.1016/j.ymben.2015.10.008CrossRefGoogle Scholar
  163. Watzer B, Engelbrecht A, Hauf W, Stahl M, Maldener I, Forchhammer K (2015) Metabolic pathway engineering using the central signal processor PII. Microb Cell Factories 14:1–12.  https://doi.org/10.1186/s12934-015-0384-4CrossRefGoogle Scholar
  164. Wu YY, Culler S, Khandurina J, Van Dien S, Murray RM (2015) Prototyping 1,4-butanediol (BDO) biosynthesis pathway in a cell-free transcription-translation (TX-TL) system. bioRxiv.  https://doi.org/10.1101/017814
  165. Xiao J, Tan J, Jiang R, He X, Xu Y, Ling Y, Luan S, Tang H (2017) A pH and redox dual responsive homopolypeptide: synthesis, characterization, and application in “smart” single-walled carbon nanotube dispersion. Polym Chem 8:7025–7032.  https://doi.org/10.1039/c7py01393kCrossRefGoogle Scholar
  166. Xu Y, Liu H, Du W, Sun Y, Ou X, Liu D (2009) Integrated production for biodiesel and 1,3-propanediol with lipase-catalyzed transesterification and fermentation. Biotechnol Lett 31:1335–1341.  https://doi.org/10.1007/s10529-009-0025-2CrossRefGoogle Scholar
  167. Xu Q, He C, Ren K, Xiao C, Chen X (2016) Thermosensitive polypeptide hydrogels as a platform for ROS-triggered cargo release with innate Cytoprotective ability under oxidative stress. Adv Healthc Mater 5:1979–1990.  https://doi.org/10.1002/adhm.201600292CrossRefGoogle Scholar
  168. Xue Y, Zhang Y, Cheng D, Daddy S, He Q (2014a) Genetically engineering Synechocystis sp. Pasteur culture collection 6803 for the sustainable production of the plant secondary metabolite p -coumaric acid. Proc Natl Acad Sci 111:9449–9454.  https://doi.org/10.1073/pnas.1323725111CrossRefGoogle Scholar
  169. Xue Y, Zhang Y, Grace S, He Q (2014b) Functional expression of an Arabidopsis p450 enzyme, p-coumarate-3-hydroxylase, in the cyanobacterium Synechocystis PCC 6803 for the biosynthesis of caffeic acid. J Appl Phycol 26:219–226.  https://doi.org/10.1007/s10811-013-0113-5CrossRefGoogle Scholar
  170. Yan L, Yang L, He H, Hu X, Xie Z, Huang Y, Jing X (2012) Photo-cross-linked mPEG-poly(γ-cinnamyl-l-glutamate) micelles as stable drug carriers. Polym Chem 3:1300–1307.  https://doi.org/10.1039/c2py20049jCrossRefGoogle Scholar
  171. Yeom S-J, Kim M, Kwon KK, Fu Y, Rha E, Park S-H, Lee H, Kim H, Lee D-H, Kim D-M, Lee S-G (2018) A synthetic microbial biosensor for high-throughput screening of lactam biocatalysts. Nat Commun 9:5053.  https://doi.org/10.1038/s41467-018-07488-0CrossRefGoogle Scholar
  172. Yu J (2018) Fixation of carbon dioxide by a hydrogen-oxidizing bacterium for value-added products. World J Microbiol Biotechnol 34:1–7.  https://doi.org/10.1007/s11274-018-2473-0CrossRefGoogle Scholar
  173. Zhang P, Shao Z, Jin W, Duan D (2016) Comparative characterization of two GDP-mannose dehydrogenase genes from Saccharina japonica (Laminariales, Phaeophyceae). BMC Plant Biol 16:1–10.  https://doi.org/10.1186/s12870-016-0750-3CrossRefGoogle Scholar
  174. Zhang A, Carroll AL, Atsumi S (2017) Carbon recycling by cyanobacteria: improving CO2fixation through chemical production. FEMS Microbiol Lett 364.  https://doi.org/10.1093/femsle/fnx165
  175. Zhao H, Sanda F, Masuda T (2006) Stimuli-responsive conjugated polymers. Synthesis and chiroptical properties of polyacetylene carrying l-glutamic acid and azobenzene in the side chain. Polymer 47:2596–2602.  https://doi.org/10.1016/j.polymer.2006.02.022CrossRefGoogle Scholar
  176. Zheng Z-M, Cheng K-K, Hu Q-L, Liu H-J, Guo N-N, Liu D-H (2008) Effect of culture conditions on 3-hydroxypropionaldehyde detoxification in 1,3-propanediol fermentation by Klebsiella pneumoniae. Biochem Eng J 39:305–310.  https://doi.org/10.1016/j.bej.2007.10.001CrossRefGoogle Scholar
  177. Zheng P, Dong JJ, Sun ZH, Ni Y, Fang L (2009) Fermentative production of succinic acid from straw hydrolysate by Actinobacillus succinogenes. Bioresour Technol 100:2425–2429.  https://doi.org/10.1016/j.biortech.2008.11.043CrossRefGoogle Scholar
  178. Zheng L, Sundaram HS, Wei Z, Li C, Yuan Z (2017) Applications of zwitterionic polymers. React Funct Polym 118:51–61.  https://doi.org/10.1016/j.reactfunctpolym.2017.07.006CrossRefGoogle Scholar
  179. Zhila N, Shishatskaya E (2018) Properties of PHA bi-, ter-, and quarter-polymers containing 4-hydroxybutyrate monomer units. Int J Biol Macromol 111:1019–1026.  https://doi.org/10.1016/j.ijbiomac.2018.01.130CrossRefGoogle Scholar
  180. Zou W, Zhu LW, Li HM, Tang YJ (2011) Significance of CO 2donor on the production of succinic acid by Actinobacillus succinogenes ATCC 55618. Microb Cell Factories 10:87.  https://doi.org/10.1186/1475-2859-10-87CrossRefGoogle Scholar

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© Springer Nature Switzerland AG 2020

Authors and Affiliations

  1. 1.Systems and Synthetic Biology Laboratory, Centre for Sustainable Future TechnologiesFondazione Istituto Italiano di TecnologiaTorinoItaly
  2. 2.Applied Science and Technology DepartmentPolitecnico di TorinoTorinoItaly

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