Synthesis of N‐Acyl‐2‐amino‐2‐deoxy‐[1‐ 14 C]‐glucoses as precursors for the biosynthesis of novel N‐acylneuraminic acids

Abstract N‐Propanoyl‐, N‐butanoyl‐, N‐pentanoyl‐, N‐hexanoyl‐, N‐heptanoyl‐ and N‐crotonoyl‐[1‐ 14 C]‐D‐glucosamine were synthesized from [1‐ 14 C]‐D‐glucosamine and their respective carbonic acid anhydrides as precursors for the biosynthesis of the corresponding N‐acyl neuraminic acids. The N‐acyl‐...

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Bibliographic Details
Published in:Journal of Labelled Compounds and Radiopharmaceuticals
Main Authors: Kayser, Holger, Zeitler, Reinhard, Hoppe, Berthold, Reutter, Werner
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 1992
Subjects:
Online Access:http://dx.doi.org/10.1002/jlcr.2580310910
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fjlcr.2580310910
https://onlinelibrary.wiley.com/doi/full/10.1002/jlcr.2580310910
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Summary:Abstract N‐Propanoyl‐, N‐butanoyl‐, N‐pentanoyl‐, N‐hexanoyl‐, N‐heptanoyl‐ and N‐crotonoyl‐[1‐ 14 C]‐D‐glucosamine were synthesized from [1‐ 14 C]‐D‐glucosamine and their respective carbonic acid anhydrides as precursors for the biosynthesis of the corresponding N‐acyl neuraminic acids. The N‐acyl‐glucosamines are phosphorylated to their respective phosphate by N‐acetyl‐glucosamine kinase in a rat liver homogenate. These precursors may become valuable tools to investigate the biological role of the N‐acyl side chain of N‐acyl‐glucosamines and N‐acyl neuraminic acids which are components of glycoconjugates.