Nucleoside Phosphonic Acids. II. The Synthesis of 5'-Deoxythymidine 5'-Phosphonic Acid and Its Pyrophosphate Derivatives^*

Staphylococcal nuclease active-site amino acids: pH dependence of tyrosines and arginines by carbon-13 NMR and correlation with kinetic studies

“…Thymidine-5'-(p-nitrophenyl phosphate) (PN-PdT) was obtained as the NH4+ salt (Sigma). Thymidine 3'-phosphate 5'-(p-nitrophenyl phosphate) (PNPdTp) was synthesized from PNPdT and cyanoethyl phosphate by the procedure of Glinski et al (1971) and purified on diethylaminoethyl-Sephadex (Pharmacia) (Rammler et al, 1967):…”

Phosphonates as analogues of natural phosphates

“…Both approaches are in common use and the reader would be well advised to be familiar with both.] The use of this approach is also claimed83 for the preparation of the corresponding isosteric phosphonic acids related to D-xylose 5-phosphate (16), o-lyxose 5-phosphate (17), D-arabinose 5-phosphate (18), 2-deoxy-D-ribose 5-phosphate (19), D-glucose 6-phosphate (20), and o-mannose 6-phosphate (21), although complete experimental details for each are not provided in the patent. More recently this same approach has been described by Adams et al87 for the preparation of 20.…”

“…reported. 20 Holy also reported121 the synthesis of 31 in 15% overall yield using tris(2-benzyloxyethyl) phosphite as the phosphorus reagent in an Arbuzov reaction. The diester was cleaved in four steps involving hydrogenolysis, iodination, alkylation, and mild hydrolysis.…”

“…For example, the UMP analogue 31 was activated by conversion to the morpholidate derivative according to the method of Moffatt and Khorana;134 this was followed by displacement with phosphate or pyrophosphate to yield the analogues 47 and 48 of UDP and UTP, respectively.120 For the corresponding dTDP and dTTP analogues, 49 and 50, sequential activation by reaction with carbonyl diimidazole followed by phosphate displacement was used. 20 The preparation of a nonisosteric analogue 51 of UDP-glucose was performed in a manner similar to that mentioned above for UTP. 135 Analogous syntheses were performed with galactose and glucuronic acid derivatives.…”

Nucleoside phosphonic acids. V. Inhibition of micrococcal nuclease with 5'-deoxythymidine-5'-phosphonic acid containing oligomers

“…In this laboratory we have been concerned with the preparation and use of nucleoside phosphonates in biological systems (Rammler et al, 1967). These substances have the advantage of not being susceptible to hydrolytic cleavage at the C5' position.…”