Literature DB >> 12837617

Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases.

Veronique Alphand1, Giacomo Carrea, Roland Wohlgemuth, Roland Furstoss, John M Woodley.   

Abstract

Biocatalysis is coming of age, with an increasing number of reactions being scaled-up and developed. The diversity of reactions is also increasing and oxidation reactions have recently been considered for scale-up to commercial processes. One important chemical conversion, which is difficult to achieve enantio- or enantiotopo- selectively, is the Baeyer-Villiger (BV) oxidation of ketones. Using cyclohexanone monooxygenase to catalyse the reaction produces optically pure esters and lactones with exquisite enantiomeric excess values. Recently, these enzymes and their many applications in synthetic chemistry have been explored. The scale-up of these conversions has been examined with the idea of implementing the first commercial Baeyer-Villiger monooxygenase-based process. Here, we review the state-of-the-art situation for the scale-up and exploitation of these enzymes.

Entities:  

Mesh:

Substances:

Year:  2003        PMID: 12837617     DOI: 10.1016/S0167-7799(03)00144-6

Source DB:  PubMed          Journal:  Trends Biotechnol        ISSN: 0167-7799            Impact factor:   19.536


  19 in total

1.  Synthesis of optically pure S-sulfoxide by Escherichia coli transformant cells coexpressing the P450 monooxygenase and glucose dehydrogenase genes.

Authors:  Jian-Dong Zhang; Ai-Tao Li; Hui-Lei Yu; Tadayuki Imanaka; Jian-He Xu
Journal:  J Ind Microbiol Biotechnol       Date:  2010-08-19       Impact factor: 3.346

2.  Crystallization and X-ray diffraction properties of Baeyer-Villiger monooxygenase MtmOIV from the mithramycin biosynthetic pathway in Streptomyces argillaceus.

Authors:  Chenchen Wang; Miranda Gibson; Jurgen Rohr; Marcos A Oliveira
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2005-10-28

3.  Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3.

Authors:  Marco Landwehr; Lisa Hochrein; Christopher R Otey; Alex Kasrayan; Jan-E Bäckvall; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

4.  Pseudomonad cyclopentadecanone monooxygenase displaying an uncommon spectrum of Baeyer-Villiger oxidations of cyclic ketones.

Authors:  Hiroaki Iwaki; Shaozhao Wang; Stephan Grosse; Hélène Bergeron; Ayako Nagahashi; Jittiwud Lertvorachon; Jianzhong Yang; Yasuo Konishi; Yoshie Hasegawa; Peter C K Lau
Journal:  Appl Environ Microbiol       Date:  2006-04       Impact factor: 4.792

5.  Bioprocess engineering to produce 9-(nonanoyloxy) nonanoic acid by a recombinant Corynebacterium glutamicum-based biocatalyst.

Authors:  Hyeonsoo Kim; Soohyun Park; Sukhyeong Cho; Jeongmo Yang; Kijun Jeong; Jinbyung Park; Jinwon Lee
Journal:  J Ind Microbiol Biotechnol       Date:  2017-06-01       Impact factor: 3.346

6.  Crystal structure of a Baeyer-Villiger monooxygenase.

Authors:  Enrico Malito; Andrea Alfieri; Marco W Fraaije; Andrea Mattevi
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-24       Impact factor: 11.205

7.  Degradation of Bis(4-Hydroxyphenyl)methane (bisphenol F) by Sphingobium yanoikuyae strain FM-2 isolated from river water.

Authors:  Daisuke Inoue; Shoji Hara; Mari Kashihara; Yusaku Murai; Erica Danzl; Kazunari Sei; Shinji Tsunoi; Masanori Fujita; Michihiko Ike
Journal:  Appl Environ Microbiol       Date:  2007-11-16       Impact factor: 4.792

8.  The genome of Polaromonas sp. strain JS666: insights into the evolution of a hydrocarbon- and xenobiotic-degrading bacterium, and features of relevance to biotechnology.

Authors:  Timothy E Mattes; Anne K Alexander; Paul M Richardson; A Christine Munk; Cliff S Han; Paul Stothard; Nicholas V Coleman
Journal:  Appl Environ Microbiol       Date:  2008-08-22       Impact factor: 4.792

9.  Overriding Traditional Electronic Effects in Biocatalytic Baeyer-Villiger Reactions by Directed Evolution.

Authors:  Guangyue Li; Marc Garcia-Borràs; Maximilian J L J Fürst; Adriana Ilie; Marco W Fraaije; K N Houk; Manfred T Reetz
Journal:  J Am Chem Soc       Date:  2018-08-13       Impact factor: 15.419

10.  Cloning, expression, characterization, and biocatalytic investigation of the 4-hydroxyacetophenone monooxygenase from Pseudomonas putida JD1.

Authors:  Jessica Rehdorf; Christian L Zimmer; Uwe T Bornscheuer
Journal:  Appl Environ Microbiol       Date:  2009-02-27       Impact factor: 4.792

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.