1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose
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| Type of Publication: | Journal article |
| URI (citable link): | http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-44085 |
| Author: | Wittmann, Valentin; Wong, Chi-Huey |
| Year of publication: | 1997 |
| Published in: | The Journal of Organic Chemistry ; 62 (1997), 7. - pp. 2144-2147. - ISSN 0022-3263. - eISSN 1520-6904 |
| DOI (citable link): | https://dx.doi.org/10.1021/jo9620066 |
| Summary: |
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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| Subject (DDC): | 540 Chemistry |
| Link to License: | Attribution-NonCommercial-NoDerivs 2.0 Generic |
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WITTMANN, Valentin, Chi-Huey WONG, 1997. 1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose. In: The Journal of Organic Chemistry. 62(7), pp. 2144-2147. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo9620066
@article{Wittmann19971HTet-9975, title={1H-Tetrazole as Catalyst in Phosphomorpholidate Coupling Reactions : Efficient Synthesis of GDP-Fucose, GDP-Mannose, and UDP-Galactose}, year={1997}, doi={10.1021/jo9620066}, number={7}, volume={62}, issn={0022-3263}, journal={The Journal of Organic Chemistry}, pages={2144--2147}, author={Wittmann, Valentin and Wong, Chi-Huey} }
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