ISSN:
0170-2041
Keywords:
CMP-sialate synthase
;
Sialic acids
;
N-Acetylneuraminic acid derivatives
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900112
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