2016年
Chemical synthesis and isolation of UDP-2-deoxy glucose and galactose
Synthetic Communications
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- 巻
- 46
- 号
- 22
- 開始ページ
- 1790
- 終了ページ
- 1795
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1080/00397911.2016.1227849
- 出版者・発行元
- Taylor and Francis Inc.
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.
- ID情報
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- DOI : 10.1080/00397911.2016.1227849
- ISSN : 1532-2432
- ISSN : 0039-7911
- SCOPUS ID : 84992213019