Nucleoside Phosphonic Acids. I. The Synthesis of 5'-Deoxyuridine 5'-Phosphonic Acids and Derivatives^*

Abstract

mer. More than one configuration of the initiatoraddase complex may be formed, only one of which is competent to initiate. The enzyme conformation for proper binding should be favored by high phosphate molarity, low temperature, and high addase specific activity. Other considerations affecting competency are the length and base composition of the initiator.

Polynucleotides containing 2'-O-methyladenosine. I. Synthesis by polynucleotide phosphorylase

“…Thus, inversion of the 2'-hydroxyl of ribose to form the arabinose derivative produced an inactive substrate (Michelson et al, 1962;Lucas-Lenard and Cohen, 1966). Conversion of either the 2'or 5'hydroxyl of the nucleoside diphosphate into the corresponding deoxy analog likewise resulted in molecules lacking substrate activity for polynucleotide phosphorylase (Grunberg-Manago, 1963;Yengoyan and Rammler, 1966). This report describes the synthesis of A'OP1 using rabbit muscle myokinase and its subsequent incorporation into large molecular weight polymers by polynucleotide phosphorylase.…”

Evidence that oxidative dephosphorylation by the nonheme Fe(II), α‐ketoglutarate:UMP oxygenase occurs by stereospecific hydroxylation

“…Interpretation of both the 1D and 2D NMR spectra of the product was also consistent with the assignment of a C‐5′ hydroxylated product (Table S1 and Figs S6‐S9). However, the low yields and degradation of the purified product—particularly to uracil and an unidentified polyhydroxylated molecule in the style of the degradation of synthetic nucleoside phosphonates that was previously reported —hindered the analytical characterization and hence conclusive identification of the product.…”

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

“…The initial neutral peak (13%) contained di-n-propyl 5'-deoxythymidine 5'-phosphonate. This material was characteristically labile to alkali (Yengoyan and Rammler, 1966). Using standard enzymatic assay conditions (see Methods), this material was completely stable to the action of the diesterase from C. adamanteus venom, Xma°H 268 µ; X^\ennH 233 µ (e :P 9100).…”

“…Paper chromatographic and electrophoretic analysis demonstrated that IX is homogeneous and its RF values and electrophoretic mobilities are consistent for a phosphonic acid (Yengoyan and Rammler, 1966).…”

“…With these uses in mind, we have initiated a systematic study of the chemistry and biochemistry of nucleoside phosphonic acids, their pyrophosphate derivatives and their polymerization products. The chemical synthesis of a ribonucleoside phosphonic acid, 5'- deoxyuridine 5'-phosphonic acid, and its pyrophosphate derivatives has been reported (Yengoyan and Rammler, 1966). In this communication, the syntheses of 5 '-deoxythymidine 5 '-phosphonic acid (I), 5'deoxythymidine 5 '-phosphonylphosphate (II), and 5'- A general method for the preparation of aliphatic phosphonates has been described (Michaelis-Arbuzov reaction; see Kosolapoff (1950) for summarizing references).…”