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Stereoselective Synthesis of a Tetrasaccharide Fragment from Cellulosome Produced by Clostridium thermocellum
Author(s) -
Zeng Yan,
Yang JinSong
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000011
Subject(s) - chemistry , tetrasaccharide , clostridium thermocellum , trisaccharide , stereochemistry , cellulosome , glycosidic bond , stereoselectivity , glycosylation , glycosyl , glycan , biochemistry , polysaccharide , catalysis , glycoprotein , cellulose , cellulase , enzyme
An efficient synthesis of a structurally congested tetrasaccharide portion from the cellulosome produced by Clostridium thermocellum has been accomplished through a stepwise glycosylation strategy. The key steps for the synthesis include the stereocontrolled construction of a range of challenging 1,2‐ cis glycosidic linkages. The 5‐ O ‐(2‐quinolinecarbonyl) substituted D‐galactofuranosyl thioglycoside 2 , 4,6‐ O ‐benzylidene protected 2‐azido‐2‐deoxyglucose thioglycoside 3 c , and 4,6‐ O ‐benzylidene protected D‐galactopyranosyl thioglycoside 4 were employed as glycosyl donors, respectively, for the high‐yielding and stereoselective formation of the corresponding 1,2‐ cis ‐α‐Gal f , α‐GlcNAc, and α‐Gal p linkages.