Enzymatic glycosylation of the topical antibiotic mupirocin

Glycoconj J. 2014 Nov;31(8):563-72. doi: 10.1007/s10719-014-9538-6. Epub 2014 Jul 30.

Abstract

Mupirocin is a commercially available antibiotic that acts on bacterial isoleucyl-tRNA synthetase, thereby inhibiting protein synthesis and preventing bacterial infection. An in vitro glycosylation approach was applied to synthesize glycoside derivatives of mupirocin using different NDP-sugars and glycosyltransferase from Bacillus licheniformis. Ultra pressure liquid chromatography-photo diode array analyses of the reaction mixtures revealed the generation of product peak(s). The results were further supported by high-resolution quadruple time of flight electrospray ionization mass spectrometry analyses. The product purified from the reaction mixture with UDP-D-glucose was subjected to NMR analysis, and the structure was determined to be mupirocin 6-O-β-D-glucoside. Other glycoside analogs of mupirocin were determined based on high-resolution mass analyses. Antibacterial activity assays against Staphylococcus aureus demonstrated complete loss of antibacterial activity after glucosylation of mupirocin at the 6-hydroxyl position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Topical
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism*
  • Anti-Bacterial Agents / pharmacology
  • Biocatalysis / drug effects
  • Chromatography, High Pressure Liquid
  • Glucosides / metabolism
  • Glycoconjugates / metabolism
  • Glycosylation / drug effects
  • Glycosyltransferases / isolation & purification
  • Glycosyltransferases / metabolism*
  • Hydrogen-Ion Concentration
  • Microbial Sensitivity Tests
  • Mupirocin / chemistry
  • Mupirocin / metabolism*
  • Mupirocin / pharmacology
  • Proton Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Time Factors

Substances

  • Anti-Bacterial Agents
  • Glucosides
  • Glycoconjugates
  • Mupirocin
  • Glycosyltransferases