Eremomycin-new glycopeptide antibiotic: Chemical properties and structure

George F. Gause, Mariya G. Brazhnikova, Nina N. Lomakina, Tatiana F. Berdnikova, Galina B. Fedorova, Nina L. Tokareva, Valeriya N. Borisova, Gyula Y. Batta

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Abstract

By a combination of chemical and spectroscopic (1H and 13C NMR) studies the structure of a glycopeptide antibiotic eremomycin has been elucidated. It is closely related to vancomycin, but differs in sugar and chlorine content. The eremomycin aglycone contains monodechlorovancomycinic acid; the only chlorine atom is situated in the second amino acid after the N-terminal amino acid residue of the peptide. The sugar part is composed of glucose and two residues of an amino sugar shown to be 2, 3, 6-trideoxy-3-amino-C-3-methyl-L-arabino-hexopyranose (4-epi-vancosamine). One of the amino sugar residues is a component of the disaccharide 2-O-(α-L-4-epi-vancosaminyl)-β-Dglucopyranose, attached to a triphenyl ether moiety; the position of another one is at the serine oxygen in the C-terminal region of the aglycone.

Original languageEnglish
Pages (from-to)1790-1799
Number of pages10
JournalThe Journal of Antibiotics
Volume42
Issue number12
DOIs
Publication statusPublished - Jan 1 1989

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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    Gause, G. F., Brazhnikova, M. G., Lomakina, N. N., Berdnikova, T. F., Fedorova, G. B., Tokareva, N. L., Borisova, V. N., & Batta, G. Y. (1989). Eremomycin-new glycopeptide antibiotic: Chemical properties and structure. The Journal of Antibiotics, 42(12), 1790-1799. https://doi.org/10.7164/antibiotics.42.1790