Development of highly potent D-glucosamine-based chiral fluorescent labeling reagents and a microwave-assisted beta-selective glycosidation of a methyl glycoside reagent.
We synthesized new chiral fluorescence labeling reagents having a 2,3-anthracenedicarboximide group from D-glucosamine, and it was possible to introduce target alcohols at the anomeric positions of the reagents with beta-selectivity by glycosidations. Especially, it was possible to use methyl glycoside reagent as a glycosyl donor with a Lewis acid and microwave irradiation, and it gave selectively beta-glycoside while the reaction without microwave irradiation gave alpha- and beta-mixed glycosides. Those reagents showed very high chiral discrimination ability, and they made it possible to separate the eight stereoisomers of 4,8,12,16-tetramethylheptadecanol by HPLC after derivatizations.
Ohrui
Hiroshi
H
Graduate School of Life Sciences, Tohoku University, Sendai. ohrui@biochem.tohoku.ac.jp
Kato
Rumiko
R
Kodaira
Teruhisa
T
Shimizu
Hiroki
H
Akasaka
Kazuaki
K
Kitahara
Takeshi
T
D002236:Carbohydrate Conformation; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D005944:Glucosamine / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006538:Heptanoic Acids / Q000737:chemistry; D008872:Microwaves; D008956:Models, Chemical; D013237:Stereoisomerism
D005456:Fluorescent Dyes; D006027:Glycosides; D006538:Heptanoic Acids; C066164:4,8,12,16-tetramethylheptanoic acid; D005944:Glucosamine