Conversion of Nocathiacin I to Nocathiacin Acid by a Mild and Selective Cleavage of Dehydroalanine
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 versatil...
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Veröffentlicht in: | Journal of organic chemistry 2007-09, Vol.72 (19), p.7447-7450 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo071115p |