A carbonate-forming Baeyer-Villiger monooxygenase

Youcai Hu; David Dietrich; Wei Xu; Ashay Patel; Justin A J Thuss; Jingjing Wang; Wen-Bing Yin; Kangjian Qiao; K N Houk; John C Vederas; Yi Tang

doi:10.1038/nchembio.1527

A carbonate-forming Baeyer-Villiger monooxygenase

Nat Chem Biol. 2014 Jul;10(7):552-4. doi: 10.1038/nchembio.1527. Epub 2014 May 18.

Authors

Affiliations

¹ Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA.
² Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada.
³ Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California, USA.
⁴ 1] Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA. [2].
⁵ 1] Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA. [2] Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California, USA.

Abstract

Despite the remarkable versatility displayed by flavin-dependent monooxygenases (FMOs) in natural product biosynthesis, one notably missing activity is the oxidative generation of carbonate functional groups. We describe a multifunctional Baeyer-Villiger monooxygenase, CcsB, which catalyzes the formation of an in-line carbonate in the macrocyclic portion of cytochalasin E. This study expands the repertoire of activities of FMOs and provides a possible synthetic strategy for transformation of ketones into carbonates.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amino Acid Sequence
Aspergillus / chemistry*
Aspergillus / enzymology
Aspergillus / genetics
Carbonates / chemistry*
Catalysis
Cytochalasins / chemistry*
Fungal Proteins / chemistry*
Fungal Proteins / genetics
Fungal Proteins / metabolism
Gene Expression Regulation, Fungal*
Gene Knockout Techniques
Genetic Complementation Test
Ketones / chemistry*
Mixed Function Oxygenases / chemistry*
Mixed Function Oxygenases / deficiency
Mixed Function Oxygenases / genetics
Oxidation-Reduction

Substances

Carbonates
Cytochalasins
Fungal Proteins
Ketones
cytochalasin E
Mixed Function Oxygenases

Associated data

PubChem-Substance/175618525
PubChem-Substance/175618526

Abstract

Publication types

MeSH terms

Substances

Associated data

Grants and funding