26184-65-6Relevant articles and documents
Chemical synthesis and isolation of UDP-2-deoxy glucose and galactose
Miyagawa, Atsushi,Takeuchi, Shunya,Itoda, Shinji,Toyama, Sanami,Kurimoto, Kenta,Yamamura, Hatsuo,Ito, Yukishige
supporting information, p. 1790 - 1795 (2016/11/18)
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.
Optimization of UDP-N-acetylmuramic acid synthesis
Humljan, Jan,Starcevic,Car,Stefanic Anderluh,Kocjan,Jenko,Urleb
, p. 102 - 106 (2008/09/21)
UDP-N-acetylmuramic acid (UDP-MurNAc) is a substrate of MurC, an important enzyme in the intracellular pathway of bacterial peptidoglycan biosynthesis. Various approaches towards preparation of UDP-Mur/VAc have been published but these synthetic preparations were shown to include many problematic steps. An optimization study with the focus on muramyl phosphate and UMP-morpholidate coupling was performed, resulting in a synthetic procedure enabling robust and easily reproducible production on a multi-gram scale.
