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Issue 5, 2017
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Stepwise cyclopropanation on the polycyclopropanated polyketide formation in jawsamycin biosynthesis

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Abstract

Jawsamycin is a polyketide–nucleoside hybrid with a unique polycyclopropane moiety on a single polyketide chain. The unexpected isolation of cyclopropane deficient jawsamycin analogs allowed us to propose a stepwise cyclopropanation mechanism for the enzymatic synthesis of this polyketide. The concise timing of the cyclopropanation could be regulated by a delicate balance between reaction rates of the condensation and cyclopropanation reactions.

Graphical abstract: Stepwise cyclopropanation on the polycyclopropanated polyketide formation in jawsamycin biosynthesis

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Supplementary files

Article information


Submitted
06 Dec 2016
Accepted
22 Dec 2016
First published
22 Dec 2016

Org. Biomol. Chem., 2017,15, 1076-1079
Article type
Communication

Stepwise cyclopropanation on the polycyclopropanated polyketide formation in jawsamycin biosynthesis

T. Hiratsuka, H. Suzuki, A. Minami and H. Oikawa, Org. Biomol. Chem., 2017, 15, 1076
DOI: 10.1039/C6OB02675C

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