Conversion of nocathiacin I to nocathiacin acid by a mild and selective cleavage of dehydroalanine |
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Authors: | Xu Libo Farthing Amy K Shi Yao-Jun Meinke Peter T Liu Kun |
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Institution: | Merck Research Laboratories, Rahway, NJ 07065, USA. libo_xu@merck.com |
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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. |
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