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Issue 4, 2009
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Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin

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Abstract

Covering: up to 2008

(+)-Zincophorin, also referred to as M144255 or griseocholin, is a polyoxygenated ionophoric antibiotic that was isolated from Streptomyces griseus in 1984. It possesses strong in vivo activity against Gram-positive bacteria and Clostridium coelchii. Its methyl ester was reported in a patent as having strong inhibitory properties against influenza WSN/virus with reduced toxicity for the host cell. Its ability to strongly bind with Zn2+, which is also present in its X-ray structure, is the basis for its name. Over the last two decades, (+)-zincophorin has attracted an impressive array of synthetic efforts including Danishefsky's first total synthesis, along with two recent elegant total syntheses reported by Cossy and Miyashita as well as our own formal total synthesis. This review provides a comparison of the different synthetic efforts on this novel mono-carboxylic acid antibiotic and documents its interesting isolation, structure determination, and biological activities.

Graphical abstract: Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin

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Article information


Submitted
29 Nov 2008
First published
11 Feb 2009

Nat. Prod. Rep., 2009,26, 560-571
Article type
Review Article

Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin

Z. Song, A. G. Lohse and R. P. Hsung, Nat. Prod. Rep., 2009, 26, 560
DOI: 10.1039/B821450F

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