A carbonate-forming Baeyer-Villiger monooxygenase.
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.
Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA.
Youcai
Y
Hu
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada.
David
D
Dietrich
Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA.
Wei
W
Xu
Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California, USA.
Ashay
A
Patel
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada.
Justin A J
JA
Thuss
Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA.
Jingjing
J
Wang
1] Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA. [2].
Wen-Bing
WB
Yin
Department of Chemical and Biomolecular Engineering, University of California-Los Angeles, Los Angeles, California, USA.
Kangjian
K
Qiao
Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, California, USA.
K N
KN
Houk
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada.
John C
JC
Vederas
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.
Yi
Y
Tang
D000595:Amino Acid Sequence; D001230:Aspergillus / Q000737:chemistry* / Q000201:enzymology / Q000235:genetics; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D003572:Cytochalasins / Q000737:chemistry*; D005656:Fungal Proteins / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism; D015966:Gene Expression Regulation, Fungal; D055786:Gene Knockout Techniques; D005816:Genetic Complementation Test; D007659:Ketones / Q000737:chemistry*; D006899:Mixed Function Oxygenases / Q000737:chemistry* / Q000172:deficiency / Q000235:genetics; D010084:Oxidation-Reduction
D002254:Carbonates; D003572:Cytochalasins; D005656:Fungal Proteins; D007659:Ketones; C007215:cytochalasin E; D006899:Mixed Function Oxygenases