Structuremodification of nucleoside anologs with the isoelectronic substitution ofborane (BH3) group for one of the nonbridging oxygens in phosphate estersincreases the lipophilicity and other properties of the phosphate innucleotides, DNA and RNA.  A general synthesisfor nucleoside P-boranomonophosphatesby H-phosphonates used in our group was briefly discussed in the recent reviewby our group (Li et al, Chem. Rev., 2007).  Here we report the H-phosphonate approach toobtain thymidine 5'-P-boranomonophosphatein a more convenient and detailed procedure. The reactions were monitored by 31P-NMR and identified byspectral data.  Hydrolysis studies ofthymidine P-boranomonophosphate by LC-MS were carried out in buffers of differentpH and temperature.  As predicted, moreacidic conditions considerably increased the hydrolysis rate.  At 22 �C and 37 �C, a seven-fold differencein rates was observed.  Based on ourstudy, we suggest that nucleoside boranomonophosphates shouldbe kept in dry form at low temperature.

Synthesis and hydrolytic properties of thymidine <i>P</i>-boranomonophosphate

242nd National Meeting (2011)

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Synthesis and hydrolytic properties of thymidine P-boranomonophosphate