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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 22
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Original Articles

Chemical synthesis and isolation of UDP-2-deoxy glucose and galactose

Atsushi MiyagawaDepartment of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi, JapanCorrespondence[email protected]
,
Shunya TakeuchiDepartment of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi, Japan
,
Shinji ItodaDepartment of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi, Japan
,
Sanami ToyamaDepartment of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi, Japan
,
Kenta KurimotoDepartment of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi, Japan
,
Hatsuo YamamuraDepartment of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya, Aichi, Japan
&
Yukishige ItoSynthetic Cellular Chemistry Laboratory, Riken, 2-1 Hirosawa, Wako, Saitama, Japan
 show all
Pages 1790-1795 | Received 30 Jun 2016, Published online: 24 Oct 2016
 
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ABSTRACT

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.

GRAPHICAL ABSTRACT

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