Synthesis of alpha-P-modified nucleoside diphosphates with ethylenediamine |
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Authors: | Li Ping Xu Zhihong Liu Hongyan Wennefors Charlotta K Dobrikov Mikhail I Ludwig János Shaw Barbara Ramsay |
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Affiliation: | Department of Chemistry, Duke University, Durham, North Carolina 27708-0346, USA. |
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Abstract: | This report describes a one-pot synthesis of alpha-P-borano-, alpha-P-thio-, and alpha-P-seleno-modified nucleoside diphosphate analogues that are otherwise difficult to obtain. The key step involves the intramolecular nucleophilic attack by an amino group in 5 to remove the gamma-phosphate. The absolute configurations of P-diastereomers were confirmed by analysis of their 1H NMR. Affinity studies revealed that the nucleoside boranodiphosphates are potentially useful in antiviral research. |
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