Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY

C Dini; N Drochon; J C Guillot; P Mauvais; P Walter; J Aszodi

doi:10.1016/s0960-894x(00)00714-9

Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY

Bioorg Med Chem Lett. 2001 Feb 26;11(4):533-6. doi: 10.1016/s0960-894x(00)00714-9.

Authors

C Dini¹, N Drochon, J C Guillot, P Mauvais, P Walter, J Aszodi

Affiliation

¹ Medicinal Chemistry Department, Aventis Pharma, Romainville, France. christophe.dini@aventis.com

PMID: 11229764
DOI: 10.1016/s0960-894x(00)00714-9

Abstract

O-beta-D-ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins that maintains enzyme inhibitory activity on MraY. A set of compounds with hydroxyl patterns different from I has been synthesized. The presence of a hydroxyl group in the 3" position is essential for the activity. The 3'-deoxy derivative (IV), however, shows a 5-fold improved potency.

MeSH terms

Aminoglycosides*
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology
Bacterial Proteins / antagonists & inhibitors*
Structure-Activity Relationship
Transferases (Other Substituted Phosphate Groups)
Transferases*

Substances

Aminoglycosides
Anti-Bacterial Agents
Bacterial Proteins
liposidomycins
Transferases
Transferases (Other Substituted Phosphate Groups)
mraY protein, Bacteria