Adenosine 2 -deoxy

N6-Ethenoderivatives of adenosine (2 -deoxy adenosine) may be obtained as metabolites from the reaction of DNA with vinyl chloride, chloroacetaldehyde or chloroethylenoxide [321]. Excitation wavelength of such heterocycles is 300 nm with a maximum of emission at 412 nm. Phosphoramidite (131) and similar compounds have been incorporated into oligonucleotides [322-324],... 

The numbering scheme used for nucleosides maintains the independence of the two structural units The pyrimidine or purine is numbered m the usual way So is the car bohydrate except that a prime symbol ( ) follows each locant Thus adenosine is a nude oside of D nbose and 2 deoxyadenosine is a nucleoside of 2 deoxy d ribose... 

By analogy with the conversion of uridine 1 into cytidines 6, the conventional amination of inosine 235a, guanosine 235b, or xanthosine 235c and their 2 -deoxy analogues to the adenosines 237 requires ... 

The susceptibilities of some of these fluorinated purine nucleosides to the action of enzymes are now described. In contrast to the inertness of the 2 -deoxy-2 -fluoro- and 3 -deoxy-3 -fluorocytidine analogs 739, 744, and 821 towards cytidine deaminase, the adenosine compounds 867, 883, and 906 are readily deaminated - by the adenosine deaminase in erythrocytes and calf intestine, but the resulting (deaminated) inosine compounds (from 867 and 883), as well as 888, are highly resistant - to cleavage by purine nucleoside phosphorylase (to give hypoxanthine base for the first two). The reason was discussed. Both 867 and 883 can form the 5 -triphosphates, without deamination, in human erythrocytes or murine sarcoma cells in the presence of 2 -deoxycoformycin, an adenosine deaminase inhibitor, but... 

GA-3-P = glyceraldehyde 3-phosphate TPP = thiamine pyrophosphate DOXP = 1-deoxy-D-syiuiose CTP = oytosine triphosphate ATP = adenosine triphosphate ... 

The analogons deamination reaction is not observed in l-methyl-2 -deoxy-adenosine nncleosides. ° Rather, in the adenine series, the Dimroth rearrangement occnrs (Scheme 8.4). On the contrary, in styrene adducts of 2 -deoxyadenosine, the hydroxyl residue of the adduct undergoes intramolecular reaction with the base to initiate deamination (Scheme 8.6). ° ° Similarly, cytosine residues bearing styrene adducts at the N3-position undergo rapid deamination (nearly complete deamination is seen within 75h). °°... 

C10H14N5O13P6)2(C10H8N2)2 Zn2 4 HaO [Adenosine 5 -zinc(II) (2,2 -bipyridyl triphosphate)]2, tetrahydrate (ATPPZN)239 C12H15N505 (5 -Deoxy-5 -adenosine-5 -yl)acetic acid (DOADAC)240 (C19H26N8O11P)(C]l3H11N3)>10 HaO Cytidylyl-(3 — 5 )-adenosine-proflavine, decahydrate (CPAPRF)241... 

C[ 1h17n o3+ I- h2o 5 -Deoxy-5 -(methylammonium)adenosine iodide, mono- MAADIM10 30 462... 

With tetrazole-A-thiocarboxylate the amino group of an OH-protected deoxy-adenosine is converted into a thiocarbamate 189 ... 

RaitVK, Zhang Q,Fabris D,et al. Conversions of formaldehyde-modified 2 -deoxy-adenosine 5 -monophosphate in conditions modeling formalin-fixed tissue dehydration. I. Histochem. Cytochem. 2006 54 301-310. 

Complete confirmation of the structures assigned to the ribonucleosides has been provided by a study of their 5-0- p -tolylsulfonyl derivatives. Whereas 2,3-O-isopropylideneuridine and 2,3-O-isopropylideneinosine give 5-p-tolylsulfonyl derivatives which, with sodium iodide, are converted to 5-deoxy-5-iodo compounds,30 31 the corresponding adenosine and cytidine... 

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