Nucleosides selective phosphorylation

Krishnan, P. Fu, Q. Lam, W. Lion, J.-Y. Dutschman, G. Cheng, Y.-C. Phosphorylation of pyrimidine deoxynucleoside analog diphosphates selective phosphorylation of L-nucleoside analog diphosphates by 3-phos-phoglycerate kinase. J. Biol. Chem., 277, 5453-5459 (2002)... 

Phosphorylation. This reagent selectively phosphorylates the terminal 5 -hydroxyl group of nucleosides, even in the presence of a 3 -hydroxyl group. The... 

Selective phosphorylation of S -hydroxy groups of nucleosides. Japanese chemists have effected selective phosphorylation of the 5 -hydroxyl group of the nucleosides... 

Taguchi, Y, Mushika, Y. 2-(Ai,V-diethylamino)-4-nitrophenyl phosphate and its use in the selective phosphorylation of unprotected nucleosides. Tetrahedron Lett. 1975, 24, 1913-1916. 

Nucleoside Acyclic Phosphates. - 2.1.1 Mononucleoside Phosphate Derivatives. A preliminary study on a novel solid phase reagent (Scheme 1) for the capture phosphorylation of nucleosides has been described. The 1 % cross-linked divinylbenzene-polystyrene copolymer, containing cyanoethoxy iV,AT-diisop-ropyl phosphine was used for the selective phosphorylation of uridine to 5 -uridine monophosphate (UMP) in 67% yield. ... 

Methods for the s)mthesis of nucleotides may be divided into four categories (1) phosphorylation of available hydroxyl groups of selectively protected nucleosides with phosphorylating agents, (2) phosphorolysis of activated nucleosides, and (3) condensation of a suitably protected... 

In most of the syntheses of ribonucleoside 5 -phosphates that we have described thus far, 2, 3 -0-isopropylidene or 2, 3 -0-benzylidene acetals of nucleosides have been employed as starting materials, to permit selective phosphorylation on 0-5. Such protecting groups, in common with acetals generally, are removable with dilute, aqueous, mineral acid. In some cases, however, the marked instability of the nucleotide derivative to acid precludes the use of these acetals, as the conditions required for removal of the acetal group are too strong. p-Substituted benzylidene derivatives (97) or (98)122.146,146 have shown utility, as deacetalation of these derivatives is readily accomplished under milder acidic conditions. A series of... 

Phosphorylation The monotriethylammonium salt of (1) reacts with an alcohol (ROH) in the presence of an acid catalyst (HOAc, TFA) and triethyl-amine in pyridine to give monoesters, R0P(0)(0H)2, in about 75-85% yield. This reaction is particularly useful for selective phosphorylation of the 5 -hydroxyl group of unprotected nucleosides. Thus adenosine can be converted into adenosine 5 -phosphate in 77% yield. 

T. (1969) Studies of phosphorylation III. Selective phosphorylation of unprotected nucleosides. Bull. Chem. Soc. 

Phosphonate esters can be readily prepared from alcohols and phosphonic acid derivatives. The selective phosphorylation of the 5 -hydroxy groups of thymidine and uridine was originally reported Mitsunobu s group in 1969. More recent examples include the modified derivative of the antitumor C-nucleoside tiazofurin (240) and an AZT triphosphate analog (241) shown... 

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