A Retrosynthesis Approach for Biocatalysis in Organic Synthesis

Chemistry : a European Journal
Rodrigo O M A de SouzaU T Bornscheuer

Abstract

For the planning of an organic synthesis route, the disconnection approach guided by retrosynthetic analysis of possible intermediates and the chemical reactions involved, back to ready available starting materials, is well established. In contrast, such concepts just get developed for biocatalytic routes. In this Review we highlight functional group interconversions catalyzed by enzymes. The article is organized rather by chemical bonds formed-exemplified for C-N, C-O- and C-C-bonds-and not by enzyme classes, covering a broad range of reactions to incorporate the desired functionality in the target molecule. Furthermore, the successful use of biocatalysts, also in combination with chemical steps, is exemplified for the synthesis of various drugs and advanced pharmaceutical intermediates such as Crispine A, Sitagliptin and Atorvastatin. This Review also provides some basic guidelines to choose the most appropriate enzyme for a targeted reaction keeping in mind aspects like commercial availability, cofactor-requirement, solvent tolerance, use of isolated enzymes or whole cell recombinant microorganisms aiming to assist organic chemists in the use of enzymes for synthetic applications.

References

Sep 1, 1989·European Journal of Biochemistry·W Hummel, M R Kula
Apr 13, 1995·Biochimica Et Biophysica Acta·B Schilling, K Lerch
Apr 1, 1997·Enzyme and Microbial Technology·M MahmoudianM J Dawson
May 13, 1998·European Journal of Biochemistry·S O SablinT P Singer
Sep 23, 1998·Trends in Biotechnology·K E Jaeger, M T Reetz
Nov 10, 1998·Trends in Biotechnology·P P TaylorI G Fotheringham
Jan 19, 1999·Applied Microbiology and Biotechnology·S Fetzner
Dec 22, 1999·Current Opinion in Biotechnology·B Schulze, M G Wubbolts
Feb 19, 2000·Current Opinion in Chemical Biology·D V JohnsonH Griengl
Feb 7, 2001·Current Opinion in Biotechnology·M ChartrainB C Buckland
Dec 5, 2000·Current Opinion in Biotechnology·O P Ward, A Singh
Feb 13, 2001·Trends in Biotechnology·F van de VeldeR A Sheldon
Feb 24, 2001·Nature·A SchmidB Witholt
Aug 21, 2001·The Journal of Organic Chemistry·R V HoffmanN Maslouh
Feb 19, 2002·Current Opinion in Biotechnology·J AltenbuchnerC Syldatk
May 15, 2002·Bioscience, Biotechnology, and Biochemistry·Tadashi FujiiHiroshi Tsunekawa
Oct 9, 2002·Angewandte Chemie·Marina AlexeevaNicholas J Turner
Mar 15, 2003·Science·Hans E SchoemakerMarcel G Wubbolts
Aug 29, 2003·Current Opinion in Biotechnology·Wilfred A van der Donk, Huimin Zhao
Sep 18, 2003·Journal of the American Chemical Society·Grace DeSantisMark J Burk
Feb 10, 2004·Angewandte Chemie·Michael BreuerThomas Zelinski
Feb 28, 2004·The Journal of Organic Chemistry·Dengjin WangWilliam A Nugent
Mar 23, 2004·Proceedings of the National Academy of Sciences of the United States of America·Ryoji NoyoriTakeshi Ohkuma
Apr 8, 2004·Proceedings of the National Academy of Sciences of the United States of America·William A GreenbergMark J Burk
Jul 16, 2004·Organic & Biomolecular Chemistry·Yutaka HondaKunisuke Izawa
Sep 9, 2004·Chemical Reviews·G-J ten BrinkR A Sheldon
Oct 9, 2004·The Journal of Organic Chemistry·Takayuki HamadaTakao Ikariya
Dec 14, 2004·Angewandte Chemie·Michael Müller
Feb 19, 2005·Chembiochem : a European Journal of Chemical Biology·Reuben CarrNicholas J Turner
Aug 9, 2005·Applied and Environmental Microbiology·Haruo MisonoShinji Nagata
Apr 15, 2006·Applied Microbiology and Biotechnology·Anne K Samland, Georg A Sprenger
May 30, 2006·Journal of Biotechnology·Chiara Carboni-OerlemansRobert van Gemert
Jan 1, 1928·The Biochemical Journal·M L Hare
Jul 14, 2006·Chemical Reviews·Kunisuke Izawa, Tomoyuki Onishi
Sep 9, 2006·Bioscience, Biotechnology, and Biochemistry·Hisashi MuramatsuNobuyoshi Esaki
Jun 19, 2007·Archives of Biochemistry and Biophysics·Dale E EdmondsonAndrea Mattevi

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Citations

Nov 28, 2017·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·Uwe T Bornscheuer
Oct 13, 2017·Angewandte Chemie·Scott P FranceNicholas J Turner
Mar 25, 2018·Angewandte Chemie·JiaJia DongWuyuan Zhang
Mar 2, 2018·Annual Review of Biochemistry·Cathleen Zeymer, Donald Hilvert
May 3, 2019·Applied Microbiology and Biotechnology·John M Woodley
Apr 5, 2019·Biotechnology Journal·Polona Žnidaršič-Plazl
Feb 23, 2019·Chembiochem : a European Journal of Chemical Biology·Arne StammPer-Olof Syrén
Feb 6, 2020·Chemistry : a European Journal·Freya TadayElaine O'Reilly
May 17, 2019·Nature Communications·Margery Cortes-ClergetBruce H Lipshutz
Jul 24, 2020·Chemical Society Reviews·Suman ChakrabartyAlison R H Narayan
Jun 20, 2020·Angewandte Chemie·Shuke WuUwe T Bornscheuer
Apr 3, 2019·ChemSusChem·Roger A Sheldon, Dean Brady
Oct 19, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mafalda Dias Gomes, John M Woodley
May 2, 2018·Biotechnology Journal·Roland Wohlgemuth
Feb 12, 2020·Communications Chemistry·Jacob E DanderNeil K Garg
Dec 17, 2020·Chemical Society Reviews·Sjoerd Slagman, Wolf-Dieter Fessner
Aug 21, 2019·Journal of Biotechnology·Sasha R DerringtonScott P France
Feb 1, 2021·Current Opinion in Biotechnology·Jovana NazorGjalt Huisman
Feb 20, 2021·Nature Catalysis·William FinniganNicholas J Turner
Dec 1, 2020·ACS Catalysis·Stefan VelikogneWolfgang Kroutil
Jun 1, 2021·ACS Catalysis·Sandro FischerAlexandria D Liang
Nov 20, 2019·Biochimica Et Biophysica Acta. Proteins and Proteomics·Rhys CutlanNicholas J Harmer
Aug 1, 2018·ACS Central Science·Alon B HensonLeroy Cronin
May 18, 2018·The Journal of Organic Chemistry·Christian R Zwick, Hans Renata
Jan 9, 2021·Journal of the American Chemical Society·Christian R ZwickHans Renata
Feb 4, 2021·ACS Central Science·Christoph K WinklerWolfgang Kroutil
Aug 31, 2021·RSC Chemical Biology·Mélanie Hall
Sep 30, 2021·Chemical Communications : Chem Comm·Yi ZhouUwe T Bornscheuer
Dec 21, 2021·Chemical Society Reviews·Ulf HanefeldCaroline E Paul

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