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Automated Electrochemical Assembly of the β‐(1,3)‐β‐(1,6)‐Glucan Hexasaccharide Using Thioglucoside Building Blocks
Author(s) -
Manmode Sujit,
Kato Moeko,
Ichiyanagi Tsuyoshi,
Nokami Toshiki,
Itoh Toshiyuki
Publication year - 2018
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.201800345
Subject(s) - chemistry , glycosidic bond , electrochemistry , combinatorial chemistry , reactivity (psychology) , anodic oxidation , carbohydrate , stereochemistry , organic chemistry , electrode , enzyme , medicine , alternative medicine , pathology
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.