Synthesis of 4-(3-azidopropoxy)phenyl glycoside of tetraarabinofuranoside related to the terminal fragment of arabinogalactan and lipoarabinomannan of mycobacteria

Synthesis of 4-(3-azidopropoxy)phenyl glycoside of tetraarabinofuranoside related to the terminal fragment of arabinogalactan and lipoarabinomannan of mycobacteria Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Вых. Данные

Год: 2024, Том: 73, Номер: 1, Страницы: 189-203 Страниц : 15 DOI: 10.1007/s11172-024-4131-z

Авторы

Abronina P.I. ¹ , Karpenko M.Yu. ¹ , Malysheva N.N. ¹ , Zinin A.I. ¹ , Myachin I.V. ¹ , Kononov L.O. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A convergent synthesis of tetraarabinofuranoside β-D-Araf-(1→2)-α-D-Araf-(1→3)-α-D-Araf-(1→5)-α-D-Araf-1↑OR (R is 4-(3-azidopropoxy)phenyl) related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria was developed. The synthesized tetraarabinofuranoside represents a linear motif of a branched hexaarabinofuranoside, which is the main LAM epitope. 4-(3-Azidopropoxy)phenyl aglycone belongs to the class of Janus aglycones, which can serve as both a temporary protective group for the anomeric position of carbohydrate and a (pre)spacer for the synthesis of neoglycoconjugates useful for the development of new tuberculosis diagnostic assays. The key step of the synthesis is the formation of 1,2-cis-glycosidic bond.

Abronina P.I. , Karpenko M.Y. , Malysheva N.N. , Zinin A.I. , Myachin I.V. , Kononov L.O.
Synthesis of 4-(3-azidopropoxy)phenyl glycoside of tetraarabinofuranoside related to the terminal fragment of arabinogalactan and lipoarabinomannan of mycobacteria
Russian Chemical Bulletin. 2024. V.73. N1. P.189-203. DOI: 10.1007/s11172-024-4131-z WOS Scopus OpenAlex

Web of science:	WOS:001175187400001
Scopus:	2-s2.0-85186420701
OpenAlex:	W4392250529

БД	Цитирований
OpenAlex	5
Scopus	6
Web of science	6