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Synthesis of both epimeric 2-deoxy-n-acetylneuraminic acids and their behaviour towards CMP-sialate synthetase-a comparison with 2-β-methylketoside of n-acetylneuraminic acid

✍ Scribed by Walther Schmid; Rudolf Christian; Erich Zbiral

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
218 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Methyl-2-R-chloro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 2 respectively methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 3 were transformed by catalytic hydrogenation or by reduction with tributyltin hydride to the corresponding 2-deoxy derivatives 4 and 5, which gave after saponification the acids 6 and 7. Both epimers are not Inhibitors of CMP-sialate synthetase (EC 2.7.7,43), whereas the 2-B-methylketoside of Neu5Ac behaves as a competitive inhibitor of the activation of Neu5Ac (N-acetylneuraminic acid). Recently the synthesis of both epimeric E-deoxy analogues of KDO (3-deoxy-

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