Guanosine diphosphate mannose (GDP-mannose) is a nucleoside diphosphate sugar, which is clinical in the production of GDP-fucose. It acts as a fucose donor in the construction of all mammalian fucosylated glycans. In mammals, fucosylated glycans play key roles in blood transfusion reactions, selectin-mediated leukocyte-endothelial adhesion, host-microbe interactions, and numerous ontogenic events like signaling events by the Notch receptor family. The focus of this presentation is to synthesize 13C labeled GDP-mannose. Isotopically labeled GDP-mannose will create a spectroscopic reference standard that will help understanding metabolomics. The synthesis involves non-enzymatic coupling between sugar-1-phosphate and nucleoside-5’-phosphate, where guanosine-5’-phosphate is activated in morpholidate form. The mechanism was first established using unlabeled material and further repeated using the [UL-13C]-labeled mannose.

Synthesis of isotopically labeled guanosine diphosphate-a-D-[UL]-13C6-mannopyranose

2019 Fall National Meeting

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