1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions: Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose | Zendy

Valentin Wittmann | Zendy; ChiHuey Wong | Zendy

Open Access

1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions: Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose

Author(s) -

Valentin Wittmann,

ChiHuey Wong

Publication year - 1997

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo9620066

Subject(s) - chemistry , tetrazole , yield (engineering) , perchloric acid , catalysis , nucleoside , pyrophosphate , acetic acid , pyridine , mannose , nucleophile , organic chemistry , medicinal chemistry , stereochemistry , materials science , metallurgy , enzyme

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 1-phosphate in the presence of 1H-tetrazole. Comparative kinetic investigations by means of (31)P NMR spectroscopy with different additives (1,2,4-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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