Functional Group Conversions by Biocatalysts

September 14th, 2010 Leave a reply »

Biocatalysis can provide alternative routes and starting materials to the process chemist, especially for chiral chemistry.   Early incorporation of a biocatalytic process may afford significant savings during the lifetime of a drug or product.  The time needed to develop a biocatalyst is becoming less and less.  Below is a list of some biocatalytic transformations that may prove useful.

Functional Group Conversions by Biocatalysts

hydrolysis of esters (lipases and esterases)

reduction of ketones to secondary alcohols (ketoreductases, aka KREDs)

reduction of polarized double bonds (ene reductases)

epoxidation of olefins (monooxygenases, peroxidases)

oxidation of ArH to ArOH (monooxygenases)

oxidation of arenes to the corresponding dihydrocatechols (dioxygenases)

Baeyer – Villager oxidation of ketones to lactones (monooxygenases)

oxidation of RCH2OH to RCHO and allylic alcohols to enones (alcohol oxidases)

removal of the p-methoxyphenyl group (PMP) from amines or imines (laccases)

halogenations, even with fluoride (halogenases)

hydration of nitriles to primary amides (nitrile hydratases)

hydrolysis of nitriles to RCO2H (nitrilases)

hydrolysis of epoxides (epoxide hydrolases)

epoxide formation from halohydrins (dehalogenases)

formation or hydrolysis of amides (peptidases)

transamination of primary amines and ketones or aldehydes (transaminases)

aldol reaction (aldolases)

cyanide addition to RCHO (hydroxynitrile lyases)

glycosidation without protecting groups (glycosidases)

References

Meyer, H.-P.; Ghisalba, O.; Leresche, J. E. Biotransformations and the Pharma Industry; Chapter 7 in Green Catalysis; Vol. 3; Anastas, P. T., Ed.; Wiley – VCH: Weinheim; 2009; pp. 171-212.

Tao, J.; Xu, J.-H. Enzymes and Their Synthetic Applications: An Overview, Chapter 1 in Biocatalysis for the Pharmaceutical Industry: Discovery, Development, and Manufacturing; Tao, J.; Lin, G.-Q.; Liese, A., Eds.; John Wiley; 2009; pp. 1-19.

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