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Synthesis of selectively protected α-(1→3)- and α-(1→5)-linked octasaccharide moiety bearing a Janus aglycone, related to the branching site of mycobacterial polysaccharides Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2022, Volume: 71, Number: 12, Pages: 2740-2750 Pages count : 11 DOI: 10.1007/s11172-022-3703-z
Authors Abronina P.I. 1 , Shvyrkina Yu.S. 1 , Zinin A.I. 1 , Chizhov A.O. 1 , Kononov L.O. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

Abstract: A novel selectively protected α-(1→3)- and α-(1→5)-linked branched octasaccharide based on arabinofuranose was synthesized via a convergent route as a glycoside with 4-(2-chloroethoxy)phenyl aglycone, belonging to the class of Janus aglycones. The obtained octasaccharide is related to the branching site of lipoarabinomannan and arabinogalactan of mycobacteria. The Janus aglycone moiety can play the role of not only a temporary protective group at the anomeric position of sugar, but also a pre-spacer for the synthesis of neoglycoconjugates useful in the design of new tools for diagnostics of tuberculosis.
Cite: Abronina P.I. , Shvyrkina Y.S. , Zinin A.I. , Chizhov A.O. , Kononov L.O.
Synthesis of selectively protected α-(1→3)- and α-(1→5)-linked octasaccharide moiety bearing a Janus aglycone, related to the branching site of mycobacterial polysaccharides
Russian Chemical Bulletin. 2022. V.71. N12. P.2740-2750. DOI: 10.1007/s11172-022-3703-z WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000971659000018
Scopus: 2-s2.0-85148940805
OpenAlex: W4322484339
Citing:
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OpenAlex 7
Scopus 7
Web of science 7
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