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 Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2018, Volume: 470, Pages: 27-35 Pages count : 9 DOI: 10.1016/j.carres.2018.10.001

Authors

Nagornaya Marina O. ^1,2 , Orlova Anna V. ² , Stepanova Elena V. ^2,3 , Zinin Alexander I. ² , Laptinskaya Tatiana V. ⁴ , Kononov Leonid O. ²

Affiliations

1	School of Advanced Manufacturing Technologies, National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk, 634050, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation
3	Research School of Chemistry & Applied Biomedical Sciences, National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk, 634050, Russian Federation
4	Faculty of Physics, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992, Moscow, Russian Federation

A new glycosyl acceptor to be used in sialylation was designed as a 3-hydroxy derivative of 4-methoxyphenyl β-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 Å, −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-α(2–3)-Gal disaccharide (78%, α:β = 13:1), which was then converted to sialyl-α(2–3)-galactose imidate building block useful for the synthesis of complex sialo-oligosaccharides.

Nagornaya M.O. , Orlova A.V. , Stepanova E.V. , Zinin A.I. , Laptinskaya T.V. , Kononov L.O.
The use of the novel glycosyl acceptor and supramer analysis in the synthesis of sialyl-α(2–3)-galactose building block
Carbohydrate Research. 2018. V.470. P.27-35. DOI: 10.1016/j.carres.2018.10.001 WOS Scopus OpenAlex

Web of science:	WOS:000449098500006
Scopus:	2-s2.0-85055097731
OpenAlex:	W2897648538

DB	Citing
OpenAlex	17
Scopus	16
Web of science	16