Biocatalytic Synthesis of Pikromycin, Methymycin, Neomethymycin, Novamethymycin, and Ketomethymycin

A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of d-desosamine and final C–H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolid...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-07, Vol.135 (30), p.11232-11238
Main Authors: Hansen, Douglas A, Rath, Christopher M, Eisman, Eli B, Narayan, Alison R. H, Kittendorf, Jeffrey D, Mortison, Jonathan D, Yoon, Yeo Joon, Sherman, David H
Format: Article
Language:English
Subjects:
Biocatalysis
Biotransformation
Lactones - metabolism
Macrolides - chemical synthesis
Macrolides - metabolism
Polyketide Synthases - metabolism
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Summary:A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of d-desosamine and final C–H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolide natural products. This methodology delivered both compound classes in 13 steps (longest linear sequence) from commercially available (R)-Roche ester in >10% overall yields.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja404134f