Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N‑Acetylneuraminic Acid

The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2016-03, Vol.81 (6), p.2607-2611
Main Authors: Williams, James T, Corcilius, Leo, Kiefel, Milton J, Payne, Richard J
Format: Article
Language:English
Subjects:
Fimbriae Proteins - chemistry
Flagellin - chemistry
Glycosylation
Gram-Negative Bacteria - chemistry
Magnetic Resonance Spectroscopy
N-Acetylneuraminic Acid - chemistry
Sugar Acids - chemical synthesis
Sugar Acids - 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:The pseudaminic acids are a family of 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids that are functional components of flagellin and pili proteins within clinically relevant Gram-negative bacteria. Herein, we describe the total synthesis of the most common pseudaminic acid, 5,7-diacetylpseudaminic acid, from N-acetylneuraminic acid. The divergent nature of the route reported here provides a robust and versatile means to access other members of the family, together with analogues, for probing the functional role of the pseudaminic acids and pseudaminic acid derived proteins in the future.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02754