Epimerization and stereochemistry of avoparcin
| Autor: | G. A. Ellestad, W. Swenson, William J. McGahren |
|---|---|
| Rok vydání: | 1983 |
| Předmět: |
Pharmacology
chemistry.chemical_classification Circular dichroism Bacteria Chemical Phenomena Chemistry Stereochemistry Avoparcin Glycopeptides Glycoside Stereoisomerism Protonation Microbial Sensitivity Tests Hydrogen-Ion Concentration Anti-Bacterial Agents Amino acid chemistry.chemical_compound Aglycone Drug Stability Drug Discovery Epimer Antibacterial activity |
| Zdroj: | The Journal of Antibiotics. 36:1683-1690 |
| ISSN: | 1881-1469 0021-8820 |
| DOI: | 10.7164/antibiotics.36.1683 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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