Automated Electrochemical Assembly of the β‐(1,3)‐β‐(1,6)‐Glucan Hexasaccharide Using Thioglucoside Building Blocks
Sujit ManmodeDepartment of Chemistry and Technology, Faculty of Engineering Tottori University 4-101 Koyamacho-minami, Tottori city 680-8552 Tottori JapanMoeko KatoDepartment of Chemistry and Technology, Faculty of Engineering Tottori University 4-101 Koyamacho-minami, Tottori city 680-8552 Tottori JapanTsuyoshi IchiyanagiFaculty of Agriculture Tottori University 4-101 Koyamacho-minami, Tottori city 680-8553 Tottori JapanToshiki NokamiCenter for Research on Green Sustainable Chemistry, Faculty of Engineering Tottori University 4-101 Koyamacho-minami, Tottori city 680-8552 Tottori JapanToshiyuki ItohCenter for Research on Green Sustainable Chemistry, Faculty of Engineering Tottori University 4-101 Koyamacho-minami, Tottori city 680-8552 Tottori Japan
2018en
ABI
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Abstract This study deals with the design, synthesis, and rational optimization of carbohydrate building blocks of glucosides for automated electrochemical assembly of β‐glucans. Oxidation potentials of building blocks with various types of protecting groups of hydroxyl groups were measured to estimate their reactivity under anodic oxidation conditions. Building blocks for both β‐1,3‐ and β‐1,6‐glycosidic linkages were optimized by an automated electrochemical assembly of disaccharides and trisaccharides. Several synthetic attempts were also made for the synthesis of the hexasaccharide repeating unit in a macrocyclic β‐glucan tridecasaccharide.
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