Synthesis of base-modified dihydropacidamycins

We describe in this paper the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-alpha,beta-L-arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5'-amino-3',5'-dideoxy-alpha-L-arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrat...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2002-04, Vol.12 (7), p.1121-1123
Main Authors: LEMOINE, Rémy C, MAGON, Angela, HECKER, Scott J
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Infective Agents - chemical synthesis
Anti-Infective Agents - chemistry
Anti-Infective Agents - pharmacology
Carbohydrate Conformation
Carbohydrates - chemistry
Chemistry
Exact sciences and technology
Organic chemistry
Peptides
Preparations and properties
Pyrimidine Nucleosides - chemical synthesis
Structure-Activity Relationship
Transferases (Other Substituted Phosphate Groups) - metabolism
Uracil - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We describe in this paper the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-alpha,beta-L-arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5'-amino-3',5'-dideoxy-alpha-L-arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrate donor was also used for the synthesis of a set of new nucleosides that were introduced in new dihydropacidamycins. These compounds were tested for biological activity, and the results showed that uracil is the only base recognized by MraY.
ISSN:0960-894X
1464-3405
DOI:10.1016/s0960-894x(02)00100-2