Development of highly potent D-glucosamine-based chiral fluorescent labeling reagents and a microwave-assisted beta-selective glycosidation of a methyl glycoside reagent.
Biosci Biotechnol Biochem
; 69(5): 1054-7, 2005 May.
Article
em En
| MEDLINE
| ID: mdl-15914934
ABSTRACT
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.
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Base de dados:
MEDLINE
Assunto principal:
Corantes Fluorescentes
/
Glucosamina
/
Glicosídeos
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article