Comparison of glycosyl donors: a supramer approach | Sciact - научная деятельность

Comparison of glycosyl donors: a supramer approach Научная публикация

Журнал

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Вых. Данные

Год: 2024, Том: 20, Страницы: 181-192 Страниц : 12 DOI: 10.3762/bjoc.20.18

Авторы

Orlova Anna V ¹ , Malysheva Nelly N ¹ , Panova Maria V ¹ , Podvalnyy Nikita M ¹ , Medvedev Michael G ² , Kononov Leonid O ¹

Организации

1	Laboratory of Glycochemistry, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation and
2	Theoretical Chemistry Group, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation

The development of new methods for chemical glycosylation commonly includes comparison of various glycosyl donors. An attempted comparison of chemical properties of two sialic acid-based thioglycoside glycosyl donors, differing only in the substituent at O-9 (trifluoroacetyl vs chloroacetyl), at different concentrations (0.05 and 0.15 mol·L−1) led to mutually excluding conclusions concerning their relative reactivity and selectivity, which prevented us from revealing a possible influence of remote protective groups at O-9 on glycosylation outcome. According to the results of the supramer analysis of the reaction solutions, this issue might be related to the formation of supramers of glycosyl donors differing in structure hence chemical properties. These results seem to imply that comparison of chemical properties of different glycosyl donors may not be as simple and straightforward as it is usually considered.

Orlova A.V. , Malysheva N.N. , Panova M.V. , Podvalnyy N.M. , Medvedev M.G. , Kononov L.O.
Comparison of glycosyl donors: a supramer approach
Beilstein Journal of Organic Chemistry. 2024. V.20. P.181-192. DOI: 10.3762/bjoc.20.18 WOS Scopus OpenAlex

Web of science:	WOS:001155879600001
Scopus:	2-s2.0-85186092602
OpenAlex:	W4391402127

БД	Цитирований
OpenAlex	3
Scopus	3
Web of science	3