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Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN

✍ Scribed by Ken-ichi Sato; Shoji Akai; Toshiyuki Hiroshima; Hidenori Aoki; Mayumi Sakuma; Ken-ju Suzuki

Book ID: 104253479
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 458 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00690-7

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✦ Synopsis

The chemoenzymatic synthesis of 13 C-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was performed by using [6-13 C]-ManNAc, [6-13 C]-Man and [3-13 C]-pyruvic acid sodium salt. In the synthesis of the compounds, 5,6-anhydro intermediates were found to easily provide not only 6-13 C-labeled but also 5-, and 6-modified NeuAc and KDN analogs. Furthermore, it was demonstrated that identical results are obtained by NMR for both [3,9-13 C]-NeuAc and 1:1 mixtures of [3-13 C]-and [9-13 C]-NeuAc.

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