title: Automated electrochemical assembly of the protected potential TMG-chitotriomycin precursor based on rational optimization of the carbohydrate building block.
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.
authors.forename: Toshiki
authors.initials: T
authors.lastname: Nokami
authors.forename: Yuta
authors.initials: Y
authors.lastname: Isoda
authors.forename: Norihiko
authors.initials: N
authors.lastname: Sasaki
authors.forename: Aki
authors.initials: A
authors.lastname: Takaiso
authors.forename: Shuichi
authors.initials: S
authors.lastname: Hayase
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Itoh
authors.affiliation: §Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Ryutaro
authors.initials: R
authors.lastname: Hayashi
authors.affiliation: §Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Shimizu
authors.affiliation: §Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D013402:Sugar Alcohols; C528826:TMG-chitotriomycin; D013865:Thioglycosides; D014312:Trisaccharides; C041161:chitotriose