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Structural variations of N ‐acetylneuraminic acid, 14. Synthesis of the β‐methyl ketosides of 4‐ oxo ‐, 7‐ oxo ‐, and 8‐ oxo‐N ‐acetylneuraminic acid and the corresponding 7,7‐ and 8,8‐dimethoxy derivatives their behaviour towards CMP‐sialate synthase
Author(s) -
Hartmann Michael,
Christian Rudolf,
Zbiral Erich
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900112
Subject(s) - chemistry , ketone , acetal , methyl ketone , sialic acid , stereochemistry , n acetylneuraminic acid , ketone bodies , organic chemistry , metabolism , biochemistry
The 4‐, 7‐, and 8‐ oxo ‐sialic acid β‐methyl ketosides 7, 10a , and 11a were obtained by transformation of easily available derivatives of N ‐acetylneuraminic acid ( 1a ). The carbonyl migration from C‐7 to C‐8 can be carried out under well‐defined conditions with formation of the ketone 11b . Starting from 7‐ and 8‐ketones 17 and 20 the corresponding dimethyl acetals are prepared. The 4‐ketone 7 behaves as a moderate competitive inhibitor of CMP‐sialate synthase [EC 2.7.7.43], whereas the 8‐ketone 11a , the 8,8‐dimethyl acetal 19 , and the 7,7‐dimethyl acetal 23 prove not to be inhibitors of this enzyme. The 7‐ketone 10a was not tested because of instability under test conditions at pH 8.5.