Skip to main content
Log in

Creating Carotenoid Diversity in E. coli Cells using Combinatorial and Directed Evolution Strategies

  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

Carotenoids represent a structurally diverse class of pigments with important biological functions and commercial applications. Biosynthesis of carotenoids has been studied on a molecular level for the core pathways and recombinant hosts have been engineered for heterologous carotenoid production. This paper summarizes our efforts on accessing novel carotenoid compounds in engineered E. coli by altering the catalytic activities of enzymes using in vitro evolution, by exploring the catalytic promiscuity of known carotenoid enzymes and by mining for novel enzymes in microbial genome sequences.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • G Armstrong, M Alberti, F Leach and JE Hearst, Nucleotide sequence, organization, and nature of the protein products of the carotenoid biosynthesis gene cluster of Rhodobacter capsulatus. Mol. Gen. Genetics 216 (1989) 286-354

    Article  Google Scholar 

  • GA Armstrong, A Schmidt, G Sandmann and JE Hearst, Genetics and biochemical characterization of carotenoid biosynthesis mutants of Rhodobacter capsulatus. J. Biol. Chem. 265 (1990) 8329-8338

    PubMed  CAS  Google Scholar 

  • F Bouvier, O Dogbo and B Camara, Biosynthesis of the food and cosmetic plant pigment bixin (annatto). Science 300 (2003a) 2089-2091

    Article  CAS  Google Scholar 

  • F Bouvier, C Suire, J Mutterer and B Camara, Oxidative remodeling of chromoplast carotenoids: identification of the carotenoid dioxygenase CsCCD and CsZCD genes involved in crocus secondary metabolite biogenesis. Plant Cell 15 (2003b) 47-62

    Article  CAS  Google Scholar 

  • G Britton, Overview of carotenoid biosynthesis. In: G Britton (ed.) Carotenoids: Biosynthesis and Metabolism. Basel: Birkhäuser (1998) pp. 13-147

    Google Scholar 

  • H Ernst, Recent advances in industrial carotenoid synthesis (vol 74. pg 2213, 2002). Pure Appl. Chem. 74 (2002) 2213-2226

    Article  CAS  Google Scholar 

  • B FernandezGonzalez, G Sandmann and A Vioque, A new type of asymmetrically acting beta-carotene ketolase is required for the synthesis of echinenone in the cyanobacterium Synechocystis sp. PCC 6803. J. Biol. Chem. 272 (1997) 9728-9733

    Article  CAS  Google Scholar 

  • G Giuliano, L Giliberto and C Rosati, Carotenoid isomerase: a tale of light and isomers. Trends Plant Sci. 7 (2002) 427-429

    Article  PubMed  CAS  Google Scholar 

  • H Kleinig, On the biosynthesis of C30 carotenoic acid glucosyl esters in Pseudomonas rhodos. Analysis of car-mutants. Z. Naturforsch. 37c (1982) 758-760

    CAS  Google Scholar 

  • H Kleinig, R Schmitt, W Meister, G Englert and H Thommen, New C30 carotenoid acid glucosyl esters from Pseudomonas rhodos. Z. Naturforsch. 34c (1978) 181-185

    Google Scholar 

  • H Krugel, P Krubasik, K Weber, H Saluz and G Sandmann, Functional analysis of genes from Streptomyces griseus involved in the synthesis of isorenieratene, a carotenoid with aromatic end groups, revealed a novel type of carotenoid desaturase. Biochim. Biophys. Acta. 1439 (1999) 57-64

    PubMed  CAS  Google Scholar 

  • PC Lee, AZR Momen, BN Mijts and C Schmidt-Dannert, Biosynthesis of structurally novel carotenoids in Escherichia coli. Chem. Biol. 10 (2003) 453-462

    Article  PubMed  CAS  Google Scholar 

  • PC Lee and C Schmidt-Dannert, Metabolic engineering towards biotechnological production of carotenoids in microorganisms. Appl. Microbiol. Biotechnol. 60 (2002) 1-11

    Article  PubMed  CAS  Google Scholar 

  • JH Marshall and GJ Wilmoth, Pigments of Staphylococcus aureus, a series of triterpenoid carotenoids. J. Bacteriol. 147 (1981a) 900-913

    CAS  Google Scholar 

  • JH Marshall and GJ Wilmoth, Proposed pathway of triterpenoid carotenoid biosynthesis in Staphylococcus aureus: evidence from a study of mutants. J. Bacteriol. 147 (1981b) 914-919

    CAS  Google Scholar 

  • BN Mijts, PC Lee and C Schmidt-Dannert, Engineering carotenoid biosynthetic pathways. Methods Enzymol. 388 (2004) 315-329

    Article  PubMed  CAS  Google Scholar 

  • BN Mijts, PC Lee and C Schmidt-Dannert, Identification of a carotenoid oxygenase synthesizing acyclic xanthophylls combinatorial biosynthesis and directed evolution. Chem. Biol. 12 (2005) 453-460

    Article  PubMed  CAS  Google Scholar 

  • BN Mijts and C Schmidt-Dannert, Engineering of secondary metabolite pathways. Curr. Opin. Biotechnol. 14 (2003) 597-602

    Article  PubMed  CAS  Google Scholar 

  • H Park, SS Kreunen, AJ Cuttriss, D DellaPenna and BJ Pogson, Identification of the carotenoid isomerase provides insight into carotenoid biosynthesis, prolamellar body formation, and photomorphogenesis. Plant Cell 14 (2002) 321-332

    Article  PubMed  CAS  Google Scholar 

  • R Petri and C Schmidt-Dannert, Dealing with complexity: evolutionary engineering and genome shuffling. Curr. Opin. Biotechnol. 15 (2004) 298-304

    Article  PubMed  CAS  Google Scholar 

  • H Pfander, M Gerspacher, M Rychener and R Schwabe, Carotenoids: Key to Carotenoids. Boston: Birkhauser (1987).

    Google Scholar 

  • G Sandmann, Combinatorial biosynthesis of carotenoids in a heterologous host: a powerful approach for the biosynthesis of novel structures. Chembiochem 3 (2002a) 629-635

    Article  CAS  Google Scholar 

  • G Sandmann, Molecular evolution of carotenoid biosynthesis from bacteria to plants. Physiol. Plantarum 116 (2002b) 431-440

    Article  CAS  Google Scholar 

  • C Schmidt-Dannert, Directed evolution of single proteins, metabolic pathways and viruses.. Biochemistry 40 (2001) 13125-13136

    Article  PubMed  CAS  Google Scholar 

  • C Schmidt-Dannert, D Umeno and FH Arnold, Molecular breeding of carotenoid biosynthetic pathways. Nat. Biotechnol. 18 (2000) 750-753

    Article  PubMed  CAS  Google Scholar 

  • G Schnurr, A Schmidt and G Sandmann, Mapping of a carotenogenic gene cluster from Erwinia herbicola and functional identification of six genes. FEMS Microbiol. Lett. 62 (1991) 157-161

    Article  PubMed  CAS  Google Scholar 

  • S Steiger, C Astier and G Sandmann, Substrate specificity of the expressed carotenoid 3,4-desaturase from Rubrivivax gelatinosus reveals the detailed reaction sequence to spheroidene and spirilloxanthin. Biochem. J. 349 (2000) 635-640

    Article  PubMed  CAS  Google Scholar 

  • Takaichi S, Oh-oka H & Madigan MT (2002) Diaponeurosporene glycoside fatty acid esters from two new alkaliphilic heliobacteria, Heliorestis. Plant Cell Physiol. 43: S29

  • S Takaichi, H Oh-Oka, T Maoka, DO Jung and MT Madigan, Novel carotenoid glucoside esters from alkaliphilic heliobacteria. Arch. Microbiol. 179 (2003) 95-100

    PubMed  CAS  Google Scholar 

  • RF Taylor, Bacterial triterpenoids.. Microbiol. Rev. 48 (1984) 181-189

    PubMed  CAS  Google Scholar 

  • D Umeno and FH Arnold, A C-35 carotenoid biosynthetic pathway. Appl. Env. Microbiol. 69 (2003) 3573-3579

    Article  CAS  Google Scholar 

  • D Umeno and FH Arnold, Evolution of a pathway to novel long-chain carotenoids. J. Bacteriol. 186 (2004) 1531-1536

    Article  PubMed  CAS  Google Scholar 

  • D Umeno, AV Tobias and FH Arnold, Evolution of the C30 carotenoid synthase crtM for function in a C40 pathway. J. Bacteriol. 184 (2002) 6690-6699

    Article  PubMed  CAS  Google Scholar 

  • D Umeno, AV Tobias and FH Arnold, Diversifying carotenoid biosynthetic pathways by directed evolution. Microb. Mol. Biol. Rev. 69 (2005) 51-78

    Article  CAS  Google Scholar 

  • AR Valla, DL Cartier and R Labia, Chemistry of natural retinoids and carotenoids: challenges for the future. Curr. Org. Synth. 1 (2004) 167-209

    Article  CAS  Google Scholar 

  • A Vershinin, Biological functions of carotenoids – diversity and evolution.. Biofactors 10 (1999) 99-104

    PubMed  CAS  Google Scholar 

  • KT Watts, BN Mijts and C Schmidt-Dannert, Current and emerging approaches for natural product biosynthesis in microbial cells. Adv. Synth. Catal. 347 (2005) 927-940

    Article  CAS  Google Scholar 

  • B Wieland, C Feil, E Gloriamaercker, G Thumm, M Lechner, JM Bravo, K Poralla and F Goetz, Genetic and biochemical analyses of the biosynthesis of the yellow carotenoid 4,4′-diaponeurosporene of Staphylococcus aureus. J. Bacteriol. 176 (1994) 7719-7726

    PubMed  CAS  Google Scholar 

  • VV Yurkov and JT Beatty, Aerobic anoxygenic phototrophic bacteria. Microb. Mol. Biol. Rev. 62 (1998) 695-724

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Claudia Schmidt-Dannert.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Schmidt-Dannert, C., Lee, P.C. & Mijts, B.N. Creating Carotenoid Diversity in E. coli Cells using Combinatorial and Directed Evolution Strategies. Phytochem Rev 5, 67–74 (2006). https://doi.org/10.1007/s11101-005-5465-2

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-005-5465-2

Keywords

Navigation