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Structural variations ofN-acetylneuraminic acid, 15. Synthesis of 9-deoxy-, 7,9-dideoxy-, and 4,7,9-trideoxy-N-acetylneuraminic acid and their behaviour towards CMP-sialate synthase

✍ Scribed by Schreiner, Erwin ;Christian, Rudolf ;Zbiral, Erich

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
545 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The methyl ester of N‐acetylneuraminic acid β‐methyl ketoside (Neu5Ac1Me‐2β‐Me) (1) is used as common starting material for the synthesis of the title compounds. Combined derivatization reactions with reagents thiophosgene, p‐cresol, benzoyl chloride, and acetic anhydride/pyridine lead to the thiocarbonate derivatives 2, 6–8, and 12. Further transformation with iodomethane yields the 9‐iodo compounds 3, 9, and 13, which are reduced by tributyltin hydride to the deoxy derivatives 4, 10, and 14. Hydrolysis of 14, 10, and 4 affords the desired 9‐deoxy, 7,9‐dideoxy‐, and 4,7,9‐trideoxy‐N‐acetylneuraminic acids 15 (9‐d‐Neu5Ac), 11 (7,9‐d~2~‐Neu5Ac), and 5 (4,7,9‐d~3~‐Neu5Ac), respectively. — The sialic acid analogues 11 and 5 were activated by CMP‐sialate synthase [E,C.2.7.7.43] to an extent of 30–40 and 50–60%, respectively, relative to N‐acetylneuraminic acid.

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