Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2020 Feb 13;11(10):2587-2605.
doi: 10.1039/c9sc05746c. eCollection 2020 Mar 14.

The Hitchhiker's guide to biocatalysis: recent advances in the use of enzymes in organic synthesis

Roger A Sheldon  1   2 , Dean Brady  1 , Moira L Bode  1
Affiliations
Review

The Hitchhiker's guide to biocatalysis: recent advances in the use of enzymes in organic synthesis

Roger A Sheldon et al. Chem Sci. .

Abstract

Enzymes are excellent catalysts that are increasingly being used in industry and academia. This perspective is primarily aimed at synthetic organic chemists with limited experience using enzymes and provides a general and practical guide to enzymes and their synthetic potential, with particular focus on recent applications.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1. Nitrile hydratase catalysed hydrations of nitriles.
Scheme 2
Scheme 2. Enzymatic kinetic resolutions using lipases.
Scheme 3
Scheme 3. Reduction and reductive amination of ketones.
Scheme 4
Scheme 4. KRED catalysed reduction of prochiral ketones.
Scheme 5
Scheme 5. Examples of enantiomerically pure secondary alcohols produced with engineered KREDs.
Scheme 6
Scheme 6. Enzymatic primary amine synthesis with amine dehydrogenases.
Scheme 7
Scheme 7. Imine reductases and amine dehydrogenase for reductive aminations with amines.
Scheme 8
Scheme 8. Enantioselective conversion of prochiral alcohols to chiral amines via hydrogen borrowing.
Scheme 9
Scheme 9. An evolved choline oxidase as a broad spectrum primary alcohol oxidase.
Scheme 10
Scheme 10. HMFA oxidation with flavin dependent AOx.
Scheme 11
Scheme 11. AOx catalysed ammoxidation of an alcohol.
Scheme 12
Scheme 12. Laccase/TEMPO catalysed oxidations of alcohols.
Scheme 13
Scheme 13. Combination of an ALDH with an ERED.
Scheme 14
Scheme 14. Enantioselective sulfoxidation using an ADH/BVMO cascade.
Scheme 15
Scheme 15. Desymmetrisation of a prochiral amine with an MAO.
Scheme 16
Scheme 16. Monooxygenase and peroxygenase pathways.
Scheme 17
Scheme 17. Olefin cis-dihydroxylation catalysed by a dioxygenase.
Scheme 18
Scheme 18. Synthesis of sitagliptin.
Scheme 19
Scheme 19. Enzymatic C–C bond forming reactions.
Scheme 20
Scheme 20. Competing biocatalytic routes to atorvastatin intermediates.
Scheme 21
Scheme 21. Biocatalytic cascade synthetic route to islatravir.
Scheme 22
Scheme 22. Stereoselective cyclopropanation reaction of P450BM3.
Scheme 23
Scheme 23. C–H aminations catalysed by Cyt P450s.
Scheme 24
Scheme 24. Olefination of aromatic aldehydes.
Scheme 25
Scheme 25. C–H fluoroalkylation of amines.
Scheme 26
Scheme 26. Addition of thiols to vinyl esters.
Scheme 27
Scheme 27. Lipase-catalysed Mannich reaction.
None
Roger A. Sheldon
None
Dean Brady
None
Moira L. Bode
See this image and copyright information in PMC

References

    1. Esquirol L., Peat T. S., Wilding M., Liu J.-W., French N. G., Hartley C. J., Onagi H., Nebl T., Easton C. J., Newman J., Scott C. J. Biol. Chem. 2018;293:7880–7891. - PMC - PubMed
    1. Delgove M. A. F., Laurent A. B., Woodley J. M., Bernaerts K. V., van der Meer Y. ChemSusChem. 2019;12:1349–1360. - PMC - PubMed
    1. Schmid A., Dordick J. S., Hauer B., Kiener A., Wubbolts M., Witholt B. Nature. 2001;409:258–268. - PubMed
    1. Straathof A. J. J., Panke S., Schmid A. Curr. Opin. Biotechnol. 2002;13:548–556. - PubMed
    1. Sheldon R. A., Brady D. Chem. Commun. 2018;54:6088–6104. - PubMed