化学
尿苷
尿苷二磷酸
糖基转移酶
尿苷二磷酸葡萄糖
半乳糖
反应性(心理学)
水解
糖
酶
有机化学
生物化学
色谱法
核糖核酸
替代医学
病理
基因
医学
作者
Atsushi Miyagawa,Shunya Takeuchi,Shinji Itoda,Sanami Toyama,Kenta Kurimoto,Hisao Yamamura,Yukishige Ito
标识
DOI:10.1080/00397911.2016.1227849
摘要
2-Deoxy sugars are attractive compounds in synthetic chemistry with regard to reactivity and stereoselectivity. Moreover, their ability to inhibit enzymes and metabolism is significant in biology. In this study, uridine-5′-diphosphate (UDP)-2-deoxy glucose (11) and galactose (12) were synthesized chemically. These sugar donors for glycosyltransferases were obtained α-selectively via phosphorylation using thioglycosides, coupling reaction with uridine-5′-monophosphate (UMP)-morpholidate, and moderate deacetylation. Isolation was carried out by sequential silica-gel chromatography using two kinds of developing solvents in a refrigerator. The structures were elucidated from the NMR results. Investigation of stability showed that the synthesized UDP-2-deoxy sugars were hydrolyzed much faster in buffer (pH 4) than the natural UDP sugars.
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