Total Synthesis of Native 5,7-Diacetylpseudaminic Acid from N-Acetylneuraminic Acid
File version
Accepted Manuscript (AM)
Author(s)
Corcilius, Leo
Kiefel, Milton J
Payne, Richard J
Griffith University Author(s)
Primary Supervisor
Other Supervisors
Editor(s)
Date
Size
File type(s)
Location
License
Abstract
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.
Journal Title
Journal of Organic Chemistry
Conference Title
Book Title
Edition
Volume
81
Issue
6
Thesis Type
Degree Program
School
Publisher link
Patent number
Funder(s)
Grant identifier(s)
Rights Statement
Rights Statement
© 2016 American Chemical Society
Item Access Status
Note
Access the data
Related item(s)
Subject
Medicinal and biomolecular chemistry
Organic chemistry
Organic chemistry not elsewhere classified