Microbial Baeyer-Villiger oxidation: stereopreference and substrate acceptance of cyclohexanone monooxygenase mutants prepared by directed evolution

Organic Letters
Marko D MihovilovicManfred T Reetz

Abstract

[reaction: see text] An array of random mutants of cyclohexanone monooxygenase (CHMO) from Acinetobacter sp. NCIMB 9871 was screened against a library of structurally diverse ketones for modifications in the substrate acceptance profile and stereopreference of the enzymatic Baeyer-Villiger biooxidation. While the set of mutant biocatalysts was initially evolved for the enantiocomplementary oxidation of 4-hydroxycyclohexanone, improved and/or divergent stereoselectivities were observed for several substrates. In addition, expanded substrate acceptance to facilitate biotransformation of sterically demanding ketones was found.

References

Apr 2, 2003·Bioorganic & Medicinal Chemistry Letters·Marko D MihovilovicPeter Stanetty
Nov 12, 2003·The Journal of Biological Chemistry·Marco W FraaijeDick B Janssen
Apr 14, 2004·Proceedings of the National Academy of Sciences of the United States of America·Manfred T Reetz
Aug 26, 2004·Proceedings of the National Academy of Sciences of the United States of America·Enrico MalitoAndrea Mattevi

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Citations

Aug 29, 2009·Applied Microbiology and Biotechnology·Yong Cheol ParkGeorge N Bennett
May 6, 2011·Chemical Reviews·Hannes LeischPeter C K Lau
May 11, 2011·Chemical Reviews·Gernot A StrohmeierMandana Gruber-Khadjawi
Oct 10, 2006·Chemical Communications : Chem Comm·Marko D MihovilovicFlorian Rudroff
Feb 23, 2010·Current Opinion in Microbiology·Dominique Böttcher, Uwe T Bornscheuer
May 16, 2009·Biotechnology Advances·J D CarballeiraJ V Sinisterra
Feb 6, 2007·Current Opinion in Chemical Biology·Vivi Joosten, Willem J H van Berkel
May 16, 2017·Chembiochem : a European Journal of Chemical Biology·Kathleen BalkeUwe T Bornscheuer
Mar 16, 2017·Chemical Communications : Chem Comm·Jian-Bo WangManfred T Reetz
Jul 19, 2012·Chemistry : a European Journal·Zhi-Gang ZhangManfred T Reetz
Oct 12, 2010·Chembiochem : a European Journal of Chemical Biology·Gonzalo de GonzaloMarco W Fraaije
Nov 17, 2010·Chembiochem : a European Journal of Chemical Biology·Diederik J Opperman, Manfred T Reetz
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Ivan A YaremenkoAlexander O Terent'ev
Sep 25, 2019·Angewandte Chemie·Jan Sietmann, Johannes M Wahl
Jun 16, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Manfred T Reetz
May 11, 2010·Journal of the American Chemical Society·Karin EngströmJan-E Bäckvall
Nov 16, 2007·The Journal of Organic Chemistry·Radka SnajdrovaMarko D Mihovilovic
Mar 7, 2008·Biochemistry·Daniel E Torres PazmiñoMarco W Fraaije
Apr 18, 2012·Journal of the American Chemical Society·Brahm J YachninAlbert M Berghuis
Jan 14, 2012·Journal of the American Chemical Society·Iakov PolyakWalter Thiel
Oct 27, 2006·The Journal of Organic Chemistry·Margaret M Kayser, Christopher M Clouthier
Oct 27, 2006·The Journal of Organic Chemistry·Christopher M ClouthierManfred T Reetz

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