Open AccessSynthesis of Mannosidase-Stable Man3 and Man4 Glycans Containing S-linked Manα1→2Man Termini
Author(s) -
Mahesh Neralkar,
Tian Li,
Richard L. Redman,
Isaac J. Krauss
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c00726
Subject(s) - mannosidase , chemistry , glycan , thio , glycosylation , anomer , stereochemistry , stereoselectivity , combinatorial chemistry , biochemistry , glycoprotein , catalysis
Oligomannose glycans are of interest as HIV vaccine components, but they are subject to mannosidase degradation in vivo . Herein, we report the synthesis of oligosaccharides containing a thio linkage at the nonreducing end. A thio-linked dimannose donor participates in highly stereoselective glycosylations to afford trimannose and tetramannose fragments. Saturation transfer difference nuclear magnetic resonance (STD NMR) studies show that these glycans are recognized by HIV antibody 2G12, and we confirm that the reducing terminal S-linkage confers complete stability against x. manihotis mannosidase.