Nokami Toshiki, Isoda Yuta, Sasaki Norihiko, Takaiso Aki, Hayase Shuichi, Itoh Toshiyuki, Hayashi Ryutaro, Shimizu Akihiro, Yoshida Jun-ichi
§Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Org Lett. 2015 Mar 20;17(6):1525-8. doi: 10.1021/acs.orglett.5b00406. Epub 2015 Mar 10.
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.
对硫代糖苷的异头芳硫基和羟基保护基进行了优化，以构建碳水化合物构建块，用于自动电化学溶液相合成具有1,4-β-糖苷键的低聚葡糖胺。优化研究包括密度泛函理论计算、氧化电位测量以及壳三糖三糖的尝试合成。使用优化后的构建块完成了受保护的潜在N,N,N-三甲基-d-葡糖胺基壳三糖霉素前体的自动合成。
