Acid-base properties and proton-speciation of vancomycin

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Abstract

The protonation-deprotonation equilibria of the glycopolypeptide antibiotic vancomycin are characterized in terms of protonation macroconstants, isoelectric point and diagram of pH-dependent species distribution. Vancomycin contains two basic and four acidic groups. Of these, dissociation of the C-terminal carboxyl group takes place separately at low pH, whereas proton binding of the two amino sites and deprotonation of the three phenolic hydroxyl groups occur between pH 5 and 13, in a highly overlapping fashion. Our study indicates for an isoelectric point of 8.30 the vancomycin molecule and an average charge of + 0.67, with the predominant existence of penta- and tetraprotonated species at physiological pH.

Original languageEnglish
Pages (from-to)261-263
Number of pages3
JournalInternational Journal of Pharmaceutics
Volume89
Issue number3
DOIs
Publication statusPublished - Feb 5 1993

Keywords

  • Acid-base properties
  • Polypeptide antibiotic
  • Protonation macroconstant
  • Vancomycin

ASJC Scopus subject areas

  • Pharmaceutical Science

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