The total synthesis of lipid I

M S VanNieuwenhze; S C Mauldin; M Zia-Ebrahimi; J A Aikins; L C Blaszczak

doi:10.1021/ja016082o

The total synthesis of lipid I

J Am Chem Soc. 2001 Jul 25;123(29):6983-8. doi: 10.1021/ja016082o.

Authors

M S VanNieuwenhze¹, S C Mauldin, M Zia-Ebrahimi, J A Aikins, L C Blaszczak

Affiliation

¹ Discovery Chemistry Research and Chemical Process Research and Development, Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, USA.

PMID: 11459476
DOI: 10.1021/ja016082o

Abstract

A total synthesis of lipid I (4), a membrane-associated intermediate in the bacterial cell wall (peptidoglycan) biosynthesis pathway, is reported. This highly convergent synthesis will enable further studies on bacterial resistance mechanisms and may provide insight toward the development of new chemotherapeutic agents with novel modes of action.

MeSH terms

Gram-Positive Bacteria / chemistry
Monosaccharides / chemical synthesis*
Oligopeptides / chemical synthesis*
Peptidoglycan / biosynthesis*
Uridine Diphosphate N-Acetylmuramic Acid / analogs & derivatives*
Uridine Diphosphate N-Acetylmuramic Acid / chemical synthesis*

Substances

Monosaccharides
Oligopeptides
Peptidoglycan
Uridine Diphosphate N-Acetylmuramic Acid
lipid I
UDP-N-acetylmuramic acid pentapeptide