| Conversion of nocathiacin I to nocathiacin acid by a mild and selective cleavage of dehydroalanine. | |
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MedLine Citation:
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PMID: 17705543 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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Libo Xu; Amy K Farthing; Yao-Jun Shi; Peter T Meinke; Kun Liu |
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Publication Detail:
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Type: Journal Article Date: 2007-08-18 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Sep |
Date Detail:
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Created Date: 2007-09-07 Completed Date: 2007-10-16 Revised Date: 2010-05-19 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7447-50 Citation Subset: IM |
Affiliation:
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Merck Research Laboratories, Rahway, NJ 07065, USA. libo_xu@merck.com |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alanine
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analogs & derivatives*,
chemistry Carboxylic Acids / chemical synthesis* Peptides / chemistry* Peptides, Cyclic / chemical synthesis* Thiazoles / chemical synthesis* |
| Chemical | |
Reg. No./Substance:
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0/Carboxylic Acids; 0/Peptides; 0/Peptides, Cyclic; 0/Thiazoles; 0/nocathiacin I; 0/nocathiacin acid; 1948-56-7/dehydroalanine; 56-41-7/Alanine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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