Document Detail


Epimerization and stereochemistry of avoparcin.
MedLine Citation:
PMID:  6662809     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The epimerization of avoparcin entities is discussed in some detail. The absolute stereochemistry of avoparcin is now known since the N-methyl terminal amino acid of the aglycone has been isolated and shown to exhibit negative optical rotation and hence has the R-configuration. The same amino acid has been isolated from an epimerized solution of avoparcin and found to have positive rotation and hence the S-configuration. A comparison is made of the CD curves of beta-avoparcin and epi-beta-avoparcin. Some discussion on the effect of protonation of the terminal N-methyl group on the antibacterial activity of avoparcin is included.
Authors:
G A Ellestad; W Swenson; W J McGahren
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of antibiotics     Volume:  36     ISSN:  0021-8820     ISO Abbreviation:  J. Antibiot.     Publication Date:  1983 Dec 
Date Detail:
Created Date:  1984-03-16     Completed Date:  1984-03-16     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0151115     Medline TA:  J Antibiot (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  1683-90     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Anti-Bacterial Agents*
Bacteria / drug effects
Chemical Phenomena
Chemistry
Drug Stability
Glycopeptides / toxicity
Hydrogen-Ion Concentration
Microbial Sensitivity Tests
Stereoisomerism
Chemical
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Glycopeptides; 37332-99-3/avoparcin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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