Automated Electrochemical Assembly of the Protected Potential TMG-chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block
Toshiki NokamiYuta IsodaNorihiko SasakiAki TakaisoShuichi HayaseToshiyuki ItohRyutaro HayashiDepartment
of Synthetic Chemistry and Biological Chemistry, Graduate School of
Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, JapanAkihiro ShimizuDepartment
of Synthetic Chemistry and Biological Chemistry, Graduate School of
Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, JapanJun‐ichi YoshidaDepartment
of Synthetic Chemistry and Biological Chemistry, Graduate School of
Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
2015en
ABI
Abstract
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.
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