Literature DB >> 21900007

Baeyer-Villiger monooxygenases in aroma compound synthesis.

Michael J Fink1, Florian Rudroff, Marko D Mihovilovic.   

Abstract

Baeyer-Villiger monooxygenases (BVMOs) are presented as highly selective and efficient biocatalysts for the synthesis of aroma lactones via kinetic resolution of 2-substituted cycloketones, exemplified with two δ-valerolactones, the jasmine lactones and their ε-caprolactone homologs. Analytical scale screens of our BVMO library ensued by preparative whole-cell biotransformations led to the identification of two enzymes (cyclohexanone monooxygenase from Arthrobacter BP2 and cyclododecanone monooxygenase from Rhodococcus SC1) perfectly suited for the task at hand: easily accessible racemic starting materials were bio-oxidized to almost enantiopure ketones and lactones in good yields (48-74%) and optical purities (ee 93% to >99%, E>100).
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 21900007     DOI: 10.1016/j.bmcl.2011.08.025

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  7 in total

1.  Engineering a lipase B from Candida antactica with efficient perhydrolysis performance by eliminating its hydrolase activity.

Authors:  Xu-Ping Wang; Peng-Fei Zhou; Zhi-Gang Li; Bo Yang; Frank Hollmann; Yong-Hua Wang
Journal:  Sci Rep       Date:  2017-03-20       Impact factor: 4.379

2.  First chemo-enzymatic synthesis of the (R)-Taniguchi lactone and substrate profiles of CAMO and OTEMO, two new Baeyer-Villiger monooxygenases.

Authors:  Florian Rudroff; Michael J Fink; Ramana Pydi; Uwe T Bornscheuer; Marko D Mihovilovic
Journal:  Monatsh Chem       Date:  2016-12-21       Impact factor: 1.451

3.  Alkyl-Substituted δ-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents.

Authors:  Anna Gliszczyńska; Damian Semba; Maryla Szczepanik; Katarzyna Dancewicz; Beata Gabryś
Journal:  Molecules       Date:  2016-09-13       Impact factor: 4.411

Review 4.  Biocatalytic Oxidation Reactions: A Chemist's Perspective.

Authors:  JiaJia Dong; Elena Fernández-Fueyo; Frank Hollmann; Caroline E Paul; Milja Pesic; Sandy Schmidt; Yonghua Wang; Sabry Younes; Wuyuan Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-03       Impact factor: 15.336

Review 5.  Rhodococcus as A Versatile Biocatalyst in Organic Synthesis.

Authors:  Hanna Busch; Peter-Leon Hagedoorn; Ulf Hanefeld
Journal:  Int J Mol Sci       Date:  2019-09-26       Impact factor: 5.923

6.  Mutations Increasing Cofactor Affinity, Improve Stability and Activity of a Baeyer-Villiger Monooxygenase.

Authors:  Hamid R Mansouri; Oriol Gracia Carmona; Julia Jodlbauer; Lorenz Schweiger; Michael J Fink; Erik Breslmayr; Christophe Laurent; Saima Feroz; Leticia C P Goncalves; Daniela V Rial; Marko D Mihovilovic; Andreas S Bommarius; Roland Ludwig; Chris Oostenbrink; Florian Rudroff
Journal:  ACS Catal       Date:  2022-09-13       Impact factor: 13.700

7.  The complete genome sequence of the nitrile biocatalyst Rhodocccus rhodochrous ATCC BAA-870.

Authors:  Joni Frederick; Fritha Hennessy; Uli Horn; Pilar de la Torre Cortés; Marcel van den Broek; Ulrich Strych; Richard Willson; Charles A Hefer; Jean-Marc G Daran; Trevor Sewell; Linda G Otten; Dean Brady
Journal:  BMC Genomics       Date:  2020-01-02       Impact factor: 3.969

  7 in total

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