Chemoenzymatic synthesis of [3,9-C]-labeled NeuAc and KDN |
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Authors: | Ken-ichi Sato Shoji AkaiToshiyuki Hiroshima Hidenori AokiMayumi Sakuma Ken-ju Suzuki |
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Institution: | Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan |
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Abstract: | The chemoenzymatic synthesis of 13C-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 6-13C]-ManNAc, 6-13C]-Man and 3-13C]-pyruvic acid sodium salt. In the synthesis of the compounds, 5,6-anhydro intermediates were found to easily provide not only 6-13C-labeled but also 5-, and 6-modified NeuAc and KDN analogs. Furthermore, it was demonstrated that identical results are obtained by NMR for both 3,9-13C]-NeuAc and 1:1 mixtures of 3-13C]- and 9-13C]-NeuAc. |
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Keywords: | carbohydrates labeling NMR |
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