Study of Sugar Diphosphate Formation via New Monophosphate Coupling Reactions
Date Issued
2010
Date
2010
Author(s)
Lin, Teng-Chi
Abstract
Diphosphate is an indispensible starting material in organism. For example, oligosaccharides are synthesized from a sugar nucleoside diphosphate and a glycosyl acceptor by glycosyltransferases. Diphosphate moiety is also an important part in the structures of Lipid I and Lipid II in the process of bacterial cell wall formation. The approaches to the sugar nucleoside diphosphate and analogues of Lipid II are impeded by the diphosphate bond formation, which often requires tedious procedure and long reaction time, albeit in low yield. So, exploration of efficient methods to get diphosphate compounds is needed.
We found that 2,4,6-triisopropylbenzenesulfonyl chloride and 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) were proper condensation reagents for diphosphate bond construction. By using MgBr2 as the chelating agent of the two monophosphate substrates, the coupling reactions proceeded efficiently. The reaction times are 5–48 hours to give conversion yields of 20–70% in our model reactions. We synthesized the GDP-pyrrolidine analogue, and found that using 2,4,6-triisopropylbenzenesulfonyl chloride is more efficient than the conventional method using morpholidate. This approach provides an alternative choice for diophosphate formation.
Subjects
diphosphate
Type
thesis
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