Automated Electrochemical Assembly of the Protected Potential TMG-chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block

The anomeric arylthio group and the hydroxyl-protecting groups of thioglycosides were optimized to construct carbohydrate building blocks for automated electrochemical solution-phase synthesis of oligoglucosamines having 1,4-β-glycosidic linkages. The optimization study included density functional t...

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Bibliographic Details
Published in:Organic letters 2015-03, Vol.17 (6), p.1525-1528
Main Authors: Nokami, Toshiki, Isoda, Yuta, Sasaki, Norihiko, Takaiso, Aki, Hayase, Shuichi, Itoh, Toshiyuki, Hayashi, Ryutaro, Shimizu, Akihiro, Yoshida, Jun-ichi
Format: Article
Language:English
Subjects:
Carbohydrates - chemical synthesis
Carbohydrates - chemistry
Molecular Structure
Streptomyces - chemistry
Sugar Alcohols - chemical synthesis
Sugar Alcohols - chemistry
Thioglycosides - chemistry
Trisaccharides - chemical synthesis
Trisaccharides - chemistry
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Summary:The anomeric arylthio group and the hydroxyl-protecting groups of thioglycosides were optimized to construct carbohydrate building blocks for automated electrochemical solution-phase synthesis of oligoglucosamines having 1,4-β-glycosidic linkages. The optimization study included density functional theory calculations, measurements of the oxidation potentials, and the trial synthesis of the chitotriose trisaccharide. The automated synthesis of the protected potential N,N,N-trimethyl-d-glucosaminylchitotriomycin precursor was accomplished by using the optimized building block.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00406