Redesigned Antibiotic for Antibiotic-Resistent Bacteria

  • Author: ChemistryViews
  • Published: 26 August 2011
  • Copyright: WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Journal of the American Chemical Society/ACS
thumbnail image: Redesigned Antibiotic for Antibiotic-Resistent Bacteria

Vancomycin is an antibiotic used only, after treatment with other antibiotics has failed. Vancomycin-resistant bacteria remodel their cell wall precursor peptidoglycan terminus from D-Ala-D-Ala to D-Ala-D-Lac. Chemically, they replace an amide with an ester, reducing the binding of vancomycin to its target 1000-fold and accounting for the loss in antimicrobial activity.

A team of scientists around Dale L. Boger, The Scripps Research Institute, La Jolla, CA, USA, have successfully reengineered vancomycin to kill antibiotic-resistant bacteria. A complementary single atom exchange in the vancomycin core structure (O→NH) to counter the single atom exchange in the cell wall precursors of resistant bacteria (NH→O), reinstates potent antimicrobial activity. Remarkably, the redesigned antibiotic binds to the mutant as well as to the wild type peptidoglycan.

This charts a rational path forward for the development of antibiotics for the treatment of vancomycin-resistant bacterial infections. Reengineered organisms to produce the material or semi-synthetic approaches to the analogue are investigated.

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