Synthesis of lipid II phosphonate analogues

Anikó Borbás; Pál Herczegh

doi:10.1016/j.carres.2011.04.024

Synthesis of lipid II phosphonate analogues

Carbohydr Res. 2011 Sep 6;346(12):1628-32. doi: 10.1016/j.carres.2011.04.024. Epub 2011 Apr 29.

Authors

Anikó Borbás¹, Pál Herczegh

Affiliation

¹ Research Group for Carbohydrates of Hungarian Academy of Sciences, University of Debrecen, PO Box 94, H-4010 Debrecen, Hungary.

PMID: 21600568
DOI: 10.1016/j.carres.2011.04.024

Abstract

Simple analogues of lipid II were synthesized from 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-thio-β-D-glucopyranose using conjugate addition onto ethylidene bisphosphonate and subsequent Wadsworth-Horner-Emmons reaction with long chain aliphatic aldehydes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry
Diphosphonates / chemistry*
Indicators and Reagents / chemical synthesis*
Magnetic Resonance Spectroscopy
Monosaccharides / chemistry
Uridine Diphosphate N-Acetylmuramic Acid / analogs & derivatives*
Uridine Diphosphate N-Acetylmuramic Acid / chemical synthesis

Substances

Aldehydes
Diphosphonates
Indicators and Reagents
Monosaccharides
Uridine Diphosphate N-Acetylmuramic Acid
muramyl-NAc-(pentapeptide)pyrophosphoryl-undecaprenol
ethylidenediphosphonic acid