1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: Efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose

被引:170
作者
Wittmann, V [1 ]
Wong, CH [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
关键词
D O I
10.1021/jo9620066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved procedure is described for the efficient and high-yield (76-91%) synthesis of nucleoside diphosphate sugars from the readily available nucleoside 5'-monophosphomorpholidate and sugar l-phosphate in the presence of VI-tetrazole, Comparative kinetic investigations by means of P-31 NMR spectroscopy with different additives (1,a,4-triazole, acetic acid, N-hydroxysuccinimide, 4-(dimethylamino)pyridine hydrochloride, perchloric acid) and mass spectrometric analysis suggest that tetrazole acts as an acid and as a nucleophilic catalyst in the pyrophosphate bond formation.
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页码:2144 / 2147
页数:4
相关论文
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