The use of the novel glycosyl acceptor and supramer analysis in the synthesis of sialyl-α(2-3)-galactose building block

The use of the novel glycosyl acceptor and supramer analysis in the synthesis of sialyl-α(2-3)-galactose building block

Detalhes bibliográficos
Parent link:Carbohydrate Research
Vol. 470.— 2018.— [P. 27-35]
Corporate Authors: Национальный исследовательский Томский политехнический университет Инженерная школа новых производственных технологий Научно-образовательный центр Н. М. Кижнера, Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий (ИШХБМТ)
Outros Autores: Nagornaya M. O. Marina Olegovna, Orlova A. V. Anna, Stepanova E. V. Elena Vladimirovna, Zinin A. I. Aleksandr Ivanovich, Laptinskaya T. V. Tatiana, Kononov L. O. Leonid Olegovich
Resumo:Title screen
A new glycosyl acceptor to be used in sialylation was designed as a 3-hydroxy derivative of 4-methoxyphenyl ?-d-galactopyranoside with 2-O-acetyl group and O-4 and O-6 protected as benzylidene acetal. Two alternative syntheses of this compound were compared. Sialylation of 3-OH group of the glycosyl acceptor with O-chloroacetylated N-trifluoroacetylneuraminic acid phenyl thioglycoside (NIS, TfOH, MeCN, MS 3?A, ?40?°C) was studied in a wide concentration range (5–150?mmol?L?1). The outcome of sialylation generally followed the predictions of supramer analysis of solutions of sialyl donor in MeCN, which was performed by polarimetry and static light scattering and revealed two concentration ranges differing in solution structure and the structures of supramers of glycosyl donor. The optimized conditions of sialylation (C?=?50?mmol?L?1) were used to synthesize protected Neu-?(2–3)-Gal disaccharide (78%, ?:??=?13:1), which was then converted to sialyl-?(2–3)-galactose imidate building block useful for the synthesis of complex sialo-oligosaccharides.
Режим доступа: по договору с организацией-держателем ресурса
Publicado em: 2018
Assuntos:
электронный ресурс
труды учёных ТПУ
neuraminic acid
glycosylation
sialylation
concentration
reactivity
supramer approach
гликозилирование
реактивность
Acesso em linha:https://doi.org/10.1016/j.carres.2018.10.001
Formato: Recurso Electrónico Capítulo de Livro
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=658770

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