3-BETA-HYDROXYSIALIC ACID GLYCOSIDES .1. CALCIUM-BINDING ABILITY AND CHEMICAL AND ENZYMATIC STABILITIES

Methyl alpha- and beta-glycosides of N-acetylneuraminic acid (Neu5Ac) and N-acetyl-3beta-hydroxyneuraminic acid (Neu5Acbeta3OH) (1-4) were prepared to evaluate their calcium-binding ability. (Methyl alpha-glucopyranosidonyl) alpha- and beta-, and 4-methylumbelliferyl alpha-glycosides of Neu5Ac and N...

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Published inChemical & pharmaceutical bulletin Vol. 40; no. 10; pp. 2728 - 2734
Main Authors OKAMOTO, K, HASEGAWA, T, TOYOMAKI, Y, YAMAKAWA, M, OKUKADO, N
Format Journal Article
LanguageEnglish
Published TOKYO Pharmaceutical Soc Japan 01.10.1992
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
ENZYMATIC STABILITY
GROWTH-INHIBITION
GLYCOSIDE
D-NEURAMINIC ACID
STRUCTURAL VARIATIONS
HYDROLYSIS
SIALOSYL CHOLESTEROL
3-BETA-HYDROXYSIALIC ACID
SIALIC-ACID
ALPHA-GLYCOSIDES
SIALIC ACID
METHYL-ESTER
CHEMICAL STABILITY
FLUOROMETRIC ASSAY
NEU5AC
FLUOROGENIC SUBSTRATE
SIALIDASE
CALCIUM-BINDING
N-ACETYLNEURAMINIC ACID
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Summary:Methyl alpha- and beta-glycosides of N-acetylneuraminic acid (Neu5Ac) and N-acetyl-3beta-hydroxyneuraminic acid (Neu5Acbeta3OH) (1-4) were prepared to evaluate their calcium-binding ability. (Methyl alpha-glucopyranosidonyl) alpha- and beta-, and 4-methylumbelliferyl alpha-glycosides of Neu5Ac and Neu5Acbeta3OH (5-10) were also synthesized for the comparison of chemical and enzymatic stabilities, respectively. Methyl beta-glycosides of Neu5Ac and Neu5Acbeta3OH, 3 and 4, respectively, showed intense calcium-binding abilities, while no such ability was observed in the corresponding alpha-glycosides, 1 and 2. The Neu5Acbeta3OH glycosides, 6, 8, and 10, showed much stronger resistance to acidic hydrolysis and sialidase digestion than the corresponding Neu5Ac glycosides, 5, 7, and 9.
ISSN:0009-2363
DOI:10.1248/cpb.40.2728