A new series of glycopeptide antibiotics incorporating a squaric acid moiety: Synthesis, structural and antibacterial studies

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Abstract

The aglycones of the antibiotics eremomycin, vancomycin and ristocetin (3, 4 and 6, respectively) were prepared by deglycosidation of the parent antibiotics with hydrogen fluoride, and complete assignation of their 1H, 13C and 15N spectra was performed. The squaric acid amide esters (11-14), were prepared from dimethyl squarate. The corresponding asymmetric diamides (16-19, 22, 23) were also synthesized using 4-phenylbenzylamine and triglycine. The advantage of the method is the high regioselectivity and that no protecting group strategy is required. Electrospray mass spectroscopic method was elaborated for the determination of the site of substitution of the modified antibiotics. The antibacterial activity of the prepared compounds is discussed in detail.

Original languageEnglish
Pages (from-to)564-582
Number of pages19
JournalJournal of Antibiotics
Volume59
Issue number9
DOIs
Publication statusPublished - Sep 1 2006

Keywords

  • Antibacterial
  • Glycopeptide antibiotics
  • Squaric acid amides
  • Synthesis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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