z-logo
Premium
Modular Synthesis of Nona‐Decasaccharide Motif from Psidium guajava Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy
Author(s) -
Zhang Yunqin,
Chen Zixi,
Huang Yingying,
He Shaojun,
Yang Xingkuan,
Wu Zhibing,
Wang Xiufang,
Xiao Guozhi
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202000992
Subject(s) - chemistry , glycosylation , polysaccharide , modular design , reagent , one pot synthesis , combinatorial chemistry , stereochemistry , chemical synthesis , biochemistry , organic chemistry , catalysis , in vitro , computer science , operating system
The synthesis of long, branched, and complex carbohydrate sequences remains a challenging task in chemical synthesis. Reported here is an efficient and modular one‐pot synthesis of a nona‐decasaccharide and shorter sequences from Psidium guajava polysaccharides, which have the potent α‐glucosidase inhibitory activity. The synthetic strategy features: 1) several one‐pot glycosylation reactions on the basis of N ‐phenyltrifluoroacetimidate (PTFAI) and Yu glycosylation to streamline the chemical synthesis of oligosaccharides, 2) the successful and efficient assembly sequences (first O3′, second O5′, final O2′) toward the challenging 2,3,5‐branched Ara f motif, 3) the stereoselective 1,2‐ cis ‐glucosylation by reagent control, and 4) the convergent [6+6+7] one‐pot coupling reaction for the final assembly of the target nona‐decasaccharide. This orthogonal one‐pot glycosylation strategy can streamline the chemical synthesis of long, branched, and complicated carbohydrate chains.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here