Uridine 5 -deoxy-, synthesis

J.-C. Wu and J. Chattopadhyaya, Michael addition reactions of a,P-ene-3 -phenylselenone of uridine. New synthesis of 2, 3 -dideoxy-riZ)o-aziridino-, 2, 3 -dideoxy-2, 3 -r feo-cyclopropyl-, and 2,2 -0-anhydro-3 -deoxy-3 -aminouridine derivatives, Tetrahedron, 45 (1989) 4507-4522. 

Shaw synthesis, 3, 109 Uridine, 2 -deoxy-5-iodo-as pharmaeeutical, 1, 160 Uridine 5 -monophosphate biosynthesis, 1, 88 Uridylic acids occurrence, 3, 142 Urispas... 

In fluorine-18 chemistry some enzymatic transformations of compounds already labelled with fluorine-18 have been reported the synthesis of 6-[ F] fluoro-L-DOPA from 4-[ F]catechol by jS-tyrosinase [241], the separation of racemic mixtures of p F]fluoroaromatic amino acids by L-amino acylase [242] and the preparation of the coenzyme uridine diphospho-2-deoxy-2-p F]fluoro-a-o-glucose from [ F]FDG-1-phosphate by UDP-glucose pyrophosphorylase [243]. In living nature compounds exhibiting a carbon-fluorine bond are very rare. 

O. Prante, K. Hamacher, H.H. Coenen, Chemo-enzymatic n.c.a. synthesis of the coenzyme uridine diphospho-2-deoxy-2-[ F]fluoro-alpha-D-glucose, J. Label. Compds Radiopharm. 42 (1999) Sill. 

Animal tissues have been reported to contain the pyrophosphor-ylase of uridine 5 -(2-acetamido-2-deoxy-a-D-galactopyranosyl pyrophosphate),253 which may be used for the synthesis of this sugar nucleotide it has also been prepared254 according to Scheme 6,... 

Experimental conditions have been found for oxidation of uridine 5 -(a-D-galactopyranosyl pyrophosphate) with D-galactose oxidase.265 The reaction product is the a-D-ga(acto-hexodialdose derivative (55). Analogous treatment of uridine 5 -(acetamido-2-deoxy-a-D-galactopy-ranosyl pyrophosphate), and subsequent reduction of the product with sodium borohydride-t, affords a convenient synthesis of the 6 -tritiated derivative.2656... 

Analogous reactions have been carried out with uridine (CXI, b series) and with l-jS-D-ribofuranosylthymine (CXI, c series).62 The latter series provided an avenue to the synthesis of 5 -methylcytidine, a nucleoside which is probably identical with that detected by Dunn60 in the ribonucleic acid of wheat germ. The thiation process has also been applied to the synthesis of 5 -fluorocytidine and 2-deoxy-5 -fluorocytidine261 from 5 -fluoro-uridine and 2-deoxy-5 -fluorouridine,209,228 respectively.2618... 

Fig. 1.—The Biosynthetic Pathway Involved in Synthesis in Bacterial Cell Walls. [The symbol UDP refers to the uridine 5-(dihydrogen pyrophosphate) group-, UTP to uridine 5 - triphosphoric acid and GNAo to the 2-aoetamido-2-deoxy-D-glucose moiety.]...

Synthesis of thymidyiate requires uridine nucleotide to be converted to the deoxy form. The substrate for Thymidyiate Synthetase is dUMP, the ] J5 jsjio. methylene-tetrahydrofolate (CH3-THF) is the "methyl" donor. This form of folate derives its carbon from serine ... 

In nucleotides, azides have been used for the introduction of amino groups into either the purine moiety, as in the synthesis of 8-aminoadenosine , or into the sugar moiety, as in the synthesis of 5-amino-5-deoxy uridine . 

The same method was applied to the synthesis of biologically active nucleosides ( )-2 -deoxy-2 -(carboxymethylene)-5 -0-trityluridine-3, 2 -)/-lactone 158 (O Scheme 42). Exposure of 2, 5 -cyclouridine derivative to the House-Blankey protocol afforded the corresponding diazo compound 156, which could be converted to the y-butyrolactone of uridine 157 in 65% yield via [1,5]-C,// insertion. Lactone 158 could be smoothly obtained by an elimination reaction with sodium hydride in 85% yield. 

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