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J Org Chem. 2007 Sep 14;72(19):7447-50. Epub 2007 Aug 18.

Conversion of nocathiacin I to nocathiacin acid by a mild and selective cleavage of dehydroalanine.

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1
Merck Research Laboratories, Rahway, NJ 07065, USA. libo_xu@merck.com

Abstract

Thiazolyl peptide antibiotic nocathiacin I (1) was converted to nocathiacin acid (4) in high yield by treatment with trifluoroacetic anhydride and pyridine in THF at room temperature. Two equipotent water-soluble amide analogues of nocathiacin I were readily prepared from this important and versatile carboxylic acid intermediate under mild peptide coupling conditions. The present method is useful for chemical derivatization of complex natural products that contain C-terminal dehydroalanine.

PMID:
17705543
DOI:
10.1021/jo071115p
[Indexed for MEDLINE]
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