1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: Efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose
1H-tetrazole as catalyst in phosphomorpholidate coupling reactions: Efficient synthesis of GDP-fucose, GDP-mannose, and UDP-galactose
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DOI：
10.1021/jo9620066
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发表时间：
1997-04-04
影响因子：
3.6
通讯作者：
Wong, CH
中科院分区：
文献类型：
--
作者：
Wittmann, V;Wong, CH
本文介绍了在VI-四唑存在下，由5 ′-单磷酸吗啉核苷酸酯和1-磷酸糖高效高产率（76-91%）合成核苷二磷酸糖的改进方法。（1，α，4-三唑，乙酸，N-羟基琥珀酰亚胺，4-（二甲氨基）吡啶盐酸盐，高氯酸）和质谱分析表明，四唑在焦磷酸键形成中充当酸和亲核催化剂。
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.