Thymidine 3 ,5 -cyclic

This reaction proceeds in poor yield without an activator [38]. In the presence of TMCS (60 mol%) cyclic thymidine 3, 5 -cyclic dimethylphospho-roamidite is formed in 95% yield. 

The structures of 1,3,2-dioxaphosphinanes of biochemical significance to have been solved by x-ray crystallography are numerous the phenyl ester of thymidine 3, 5 -cyclic phosphate is an example <75PNA(72)1335, 87JA4058>. In the 1,3,5-dioxaphosphinane series, conformational studies by NMR have been supported by x-ray crystal structures <87IZV418>. 

Abbreviations used NAD+ = nicotinamide adenine dinucleotide NADH e reduced nicotinamide adenine dinucleotide NADP = nicotinamide adenine dinudeotide phosphate NAD PH reduced nicotinamide adenine dinucleotide phosphate NMN, NMN+ nicotinamide mononucleotide NMNH2 = reduced nicotinamide mononucleotide a-NAD a-nicotinamide adenine dinucleotide AMP = 5 -adenylic acid 3,5 -AMP adenosine 3, 5 -cycIic phosphate 3 ,5 -UMP = uridine 3, 5 -cyclic phosphate 3, 5 -CMP cytidine 3, 5-cyclic phosphate 3 f5 GMP = guanosine 3 5f-cyclic phosphate 3, 5 TMP thymidine 3, 5 -cyclic phosphate Dibutyryl-3, 5 -AMP = N6,02-dibutyryladenosine 3, 5 -cyclic phosphate 2, 3 -UMP = uridine 2 ,3 -cyclic monophosphate 2, 3 -CMP cytidine 2, 3 -cyclic monophosphate 2, 3 -AMP = adenosine 2, 3 -cyclic monophosphate 2 ,3 -GMP = guanosine 2 3 -cyclic monophosphate 2 -UMP = uridine 2 -phosphate -UMP uridine -phosphate 5 -UMP = uridine 5 phosphate Poly U polyuridylic acid ADP = adenosine 5 -diphosphate FAD = flavin adenine dinucleotide UpA, UpU, ApU and ApA x dinucleoside phosphates of uridine and/or adenine. c See original references for experimental conditions and additional data. 

Ci2Hi8N20iOf Methyl uridine-5-oxyacetate monohydrate, 41B, 516 C12H18N3O6P, Thymidine 3, 5 -cyclic N,N-dimethylphosphoramidate,... 

Since it is well established that the P-chiral phosphorothio-ates serve as effective probes in mechanistic studies for the phos-phoryl group transfer enzymes /16/, we turned our attention to the application of diastereomeric 8 (B=Thy, Ar=pN02C6Hi -,/17f) to elucidate the mode of action of spleen phosphodiesterase (SPDE, EC 3.1.1. 18). This enzyme splits the phosphodiester bonds to yield nucleoside 3 -phosphates. In the case of it was expected that its SPDE-catalyzed hydrolysis in 180 H 2O medium leads to P-chiral thymidine 3 - 180 phosphorothioate. On the contrary to our expectation the main product of this reaction was thymidine cyclic 3 ,5 - Rp phosphorothioate (10) /6/. By treatment of 8 under the same conditions, but in the absence of the enzyme, no trace of J 0 was detected. ... 

PMR Measurements of Chair-Twist Conformational Equilibria for Diastereomeric P-Derivatives of Thymidine Cyclic 3, 5 -Monophosphate... 

We have examined by PMR the conformational properties of certain P-derivatized thymidine cyclic nucleotides, I, and have compared them to those for the model compounds, II (3, 4). The... 

The phosphinic acid analogue 200 of cyclic AMP has been prepared by linking adenine to a cyclic methyl phosphinate derived from di-O-isopropylidene-glucose (Chapter 17). Thymidine cyclic 3, 5 -phosphorofluoridate and its sulfur analogue (201, X = O or S), as 1 1 mixtures of diastereomers, have been prepared by oxidation or sulfurization of the cyclic phosphorofluoridite. 7-Deoxypac-litaxel has been linked to cyclic AMP as a phosphotriester the product showed enhanced cytotoxicity against human cancer cells. ... 

Thymidine cyclic 3, 5 -(hydrogen phosphate), 9C1. Cyclic 3, 5 -thymidylic acid [6453-60-7]... 

Thymidine cyclic 3, 5 -(methylphosphate), C-165 Thymidine diphosphate, T-105 Thymidine 3, 5 -diphosphate, T-106 Thymidine 3 -phosphaie, T-107 Thymidine 5 -phosphate, T-108... 

A review of P-n.m.r. spectra of chair-twist conformational equilibria for diastereoisomeric phosphorus derivatives of thymidine cyclic 35 -monophosphate has appeared. 

Bentrude, W G., Sopchik, A, E, and Gajda. T. (1989) Stereo-and regio-chem-istries of the oxidations of 2-methoxy-5-t rr-butyl-l,3,2-dioxaphosphorinanes and the cyclic methyl 3, 5 -phosphite of thymidine by H2O/I2 and O2/AIBN to P-chiral phosphates. NMR assigment of phosphorus configuration to the diastereomeric thymidine cyclic methyl 3, 5 -monophosphates. J, Am, Chem. Soc, 111,3981-3987... 

Grivell, A.R. Jackson, J.F. Thymidine phosphotransferase and nucleotide phosphohydrolase of the fern Asplenium nidus. General properties and inhibition by adenosine 3 5-cyclic monophosphate. Biochem. J., 155, 571-581 (1976)... 

The configurations of the cyclic thymidine 3, 5 -[170, 180]-monophosphates can be conveniently assigned by 170 NMR spectroscopy. We have previously reported that in aqueous solution at 95° C the 170 NMR chemical shifts of the phosphoryl oxygens of cyclic 2 -deoxyadenosine 3, 5 -[170, 180]monophosphate are sufficiently different at 36.6 MHz such that two resonances can be resolved in a racemic mixture of the diastereomers, with the down-... 

The fact that the trans fusion of the thymidine-based systems appears to have little effect on the chair J twist equilibrium suggests strongly that like the model systems, the cyclic nucleotide AG°5 values for chair twist interconversions like VII - VIII or XII - XIII are only 1 to 2 kcal/mol. It seems very likely that similar values for chair-twist isomerizations of the natural cyclic nucleotides such as cAMP and cGMP (Z = X = 0 or 0) can be expected. (See e.g. XIII - XIV.)... 

The non-specific tritiation of papaverine ha been described,13 as have methods for the detection of the alkaloid in body fluids.1415 The effects of papaverine on the biochemical fate of thymidine phosphate in the thymus,16 on cyclic AMP and the uptake of calcium in isolated pig auricle,17 on the monosynaptic reflex,18 on the L-DOPA-influenced secretion of GH and PRL,19 on cerebral blood flow,20 and on longitudinal smooth muscle21 have been studied, as have the /3-receptor-stimulant... 

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