Abstract: 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.

Cite: 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

Identifiers:

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

Citing:

DB	Citing
OpenAlex	5
Scopus	6
Web of science	6

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