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Differences in reactivity of N-acetyl- and N,N-diacetylsialyl chlorides caused by their different supramolecular organization in solutions Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2017, Volume: 66, Number: 11, Pages: 2173-2179 Pages count : 7 DOI: 10.1007/s11172-017-1999-x
Authors Orlova A.V. 1 , Laptinskaya T.V. 2 , Bovin N.V. 3 , Kononov L.O. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2 Department of Physics, M. V. Lomonosov Moscow State University, Moscow, Russian Federation
3 M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: O-Sialylation of a substituted indolin-3-one under phase-transfer catalysis conditions, which does not occur when N-acetylsialyl chloride is used, proceeds with N,N-diacetylsialyl chloride as the glycosyl donor. A study using dynamic light scattering of solutions of both sialyl chlorides under conditions close to the conditions used for glycosylation showed a difference in the correlation radii of light scattering particles in such solutions. This suggests that the introduction of an additional N-acetyl group into the sialyl chloride significantly alters the structure of the supramers of glycosyl donor, which apparently have an increased accessibility of individual molecules for the attack by a nucleophile, which increases its reactivity.
Cite: Orlova A.V. , Laptinskaya T.V. , Bovin N.V. , Kononov L.O.
Differences in reactivity of N-acetyl- and N,N-diacetylsialyl chlorides caused by their different supramolecular organization in solutions
Russian Chemical Bulletin. 2017. V.66. N11. P.2173-2179. DOI: 10.1007/s11172-017-1999-x WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000427628900029
Scopus: 2-s2.0-85043976025
OpenAlex: W2790035035
Citing:
DB Citing
OpenAlex 20
Scopus 20
Web of science 18
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