A Janus Aglycone-Based Divergent Strategy for the Synthesis of the PGL-I Epitopes Ready for Conjugation

A Janus Aglycone-Based Divergent Strategy for the Synthesis of the PGL-I Epitopes Ready for Conjugation Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2026, Volume: 28, Number: 40, Pages: 12791–12796 Pages count : DOI: 10.1021/acs.orglett.6c03850

Authors

Novosad Bogdan L. ¹ , Zinin Alexander I. ¹ , Kolotyrkina Natalya G. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

An efficient synthesis of epitopes of PGL-I glycolipids of Mycobacterium leprae was achieved using the 4-methoxyphenyl (MP) group as dual-mode Janus aglycone. Cleavage of the MP aglycone in a disaccharide gave a hemiacetal precursor of the glycosyl donor that was used for the assembly of the trisaccharide PGL-I epitope through α-selective [2+1] rhamnosylation (96:4 α:β). Selective demethylation of the MP aglycone in di- and trisaccharides followed by alkylation of the resulting phenolic hydroxy group gave diverse spacer aglycones suitable for the synthesis of neoglycoconjugates.

Novosad B.L. , Zinin A.I. , Kolotyrkina N.G. , Kononov L.O.
A Janus Aglycone-Based Divergent Strategy for the Synthesis of the PGL-I Epitopes Ready for Conjugation
Organic Letters. 2026. V.28. N40. P.12791–12796. DOI: 10.1021/acs.orglett.6c03850 WOS Scopus OpenAlex

Submitted:	Aug 30, 2026
Accepted:	Sep 21, 2026
Published online:	Sep 25, 2026

≡ Web of science:	WOS:001887230200001
≡ Scopus:	2-s2.0-105052796705
≡ OpenAlex:	W7214287867