Synthesis of P-1-Citronellyl-P-2-alpha-D-pyranosyl pyrophosphates as potential substrates for the E-coli Undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG

Authors
Cudic, P Behenna, DC Yu, MK Kruger, RG Szewczuk, LM McCafferty, DG
Citation
P. Cudic et al., Synthesis of P-1-Citronellyl-P-2-alpha-D-pyranosyl pyrophosphates as potential substrates for the E-coli Undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG, BIOORG MED, 11(24), 2001, pp. 3107-3110
Citations number
23
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
11
Issue
24
Year of publication
2001
Pages
3107 - 3110
Database
ISI
SICI code
0960-894X(200112)11:24<3107:SOPPAP>2.0.ZU;2-R
Abstract
P-1-Citronellyl-P-2-alpha -D-pyranosyl pyrophosphates containing alpha -D-N -acetylglucoseaminyi. alpha -D-glucosyl, and alpha -D-N-acetylmuramyl carbo hydrates were synthesized and used in substrate specificity studies of the Escherichia coli MurG enzyme. Oxalyl chloride activation or citronellyl pho sphate for coupling to alpha -D-pyranose-1-phosphates resulted in markedly improved yields over traditional Khorana-Moffatt and diphenyl chlorophospha te activation strategies. (C) 2001 Elsevier Science Ltd. All rights reserve d.