Synthesis of an orthogonally protected precursor to the glycan repeating unit of the bacterial cell wall

S L Saha; M S Van Nieuwenhze; W J Hornback; J A Aikins; L C Blaszczak

doi:10.1021/ol016692t

Synthesis of an orthogonally protected precursor to the glycan repeating unit of the bacterial cell wall

Org Lett. 2001 Nov 1;3(22):3575-7. doi: 10.1021/ol016692t.

Authors

S L Saha¹, M S Van Nieuwenhze, W J Hornback, J A Aikins, L C Blaszczak

Affiliation

¹ Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, USA.

PMID: 11678712
DOI: 10.1021/ol016692t

Abstract

[reaction: see text]. A synthesis of stereochemically pure and orthogonally protected N-acetyl-(2-deoxy-2-aminoglucopyranosyl)-beta-[1,4]-N-acetylmuramyl (NAG-NAM) monopeptide (2), the glycopeptide core of lipid II and of the bacterial cell wall repeating unit, is reported.

MeSH terms

Bacteria / chemistry*
Cell Wall / chemistry
Disaccharides / chemical synthesis*
Diterpenes / chemical synthesis*
Indicators and Reagents
Oxidation-Reduction
Peptidoglycan / chemistry*

Substances

11-epi-helioporin B
Disaccharides
Diterpenes
Indicators and Reagents
Peptidoglycan