Biocatalytic concepts for synthesizing amine bulk chemicals: recent approaches towards linear and cyclic aliphatic primary amines and ω-substituted derivatives thereof
- 218 Downloads
In this mini-review, an overview about various developed strategies for accessing industrially relevant primary n-alkyl amines via reductive amination by means of amine dehydrogenases as well as transaminases is given. Such transformations were combined with in situ cofactor recycling methodologies avoiding the need for addition of external stoichiometric amounts of organic co-substrates. These methods comprise the application of natural photosynthesis with algae when using carbonyl compounds as substrates as well as the utilization of alcohols as substrates in combination with self-sufficient biocatalytic systems. As such a feature is of utmost importance for large-scale biotransformations in the field of bulk chemicals, which represent high-volume but low-price chemicals, the achievements open up a perspective for biocatalysis also in the area of commodity chemicals. Besides approaches to n-alkyl amines and cyclohexylamine, recently also biocatalytic cascades towards n-alkyl amines bearing functionalities in the ω-position such as a carboxylic acid ester or amino group were reported. It is noteworthy that for ω-aminolauric acid, such a process has already been demonstrated on pilot plant scale.
KeywordsAmines Amine dehydrogenases Industrial chemicals Reductive amination Transaminases, transamination
This study was funded by the Fachagentur Nachwachsende Rohstoffe (FNR) and the German Federal Ministry of Food and Agriculture (BMEL), respectively, within the funding program on the utilization of biorenewables (grant number: 22001716).
Compliance with ethical standards
Conflict of interest
The author declares that he has no conflict of interest.
This article does not contain any studies with human participants or animals performed by the author.
- Chen FF, Liu YY, Zheng GW, Xu JH (2015) Asymmetric Amination of Secondary Alcohols by using a Redox‐Neutral Two‐Enzyme Cascade. ChemCatChem 7:3838–3841.Google Scholar
- Drauz K, Gröger H, May O (eds) (2012) Enzyme catalysis in organic synthesis, vol 1–3, 3rd edn. Wiley-VCH, WeinheimGoogle Scholar
- Evonik Industries AG (2013) An alternative raw material for polyamide 12: Evonik is operating a pilot plant for bio-based ω-amino lauric acid. Press Release, July 30Google Scholar
- Löwe J, Siewert A, Scholpp AC, Wobbe L, Gröger H (2018b) Providing reducing power by microalgal photosynthesis: a novel perspective towards sustainable biocatalytic production of bulk chemicals exemplified for aliphatic amines. Sci Rep 8:10436. https://doi.org/10.1038/s41598-018-28755-6 CrossRefPubMedPubMedCentralGoogle Scholar
- Oenbrink G, Schiffer T (2009) Cyclododecanol, cyclododecanone, and laurolactam. In: Ullmann’s encyclopedia of industrial chemistry, 6th edn. Electronic release. Wiley-VCH, WeinheimGoogle Scholar
- Roose P, Eller K, Henkes E, Rossbacher R, Höke H (2015) Amines, aliphatic. In: Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim, p 1–55Google Scholar
- Weissermehl K, Arpe HJ (2010) Industrial organic chemistry, 5th edn. Wiley-VCH, WeinheimGoogle Scholar