2’-Deoxy ribonucleoside

Friedman, O. M., G. N. Mahapatra, and R. Stevenson. 1963. The Methylation of Deoxy-ribonucleosides by Diazomethane. Biochem. Biophys. Acta 68, 144. 

In view of the difficulty of hydrolyzing the pyrimidine nucleosidic linkages, ribonucleic acids have been hydrolyzed to a mixture of purine bases and pyrimidine nucleotides which is then separated by paper chromatography.132, 163 164 This method has been employed extensively for the analysis of ribonucleic acids, and gives reproducible results,166 but it has not been used to any great extent for deoxyribonucleic acids, probably because, under these conditions of hydrolysis, they yield some pyrimidine deoxy-ribonucleoside diphosphates.166... 

Figure 20.13 Summary of the reactions by which all four deoxy-ribonucleoside triphosphates can be synthesised from the nucleosides, adenosine and uridine. The reactions are summaries of the processes presented in Figures 20.8, 20.9 and 20.12. AMP is converted to IMP by a deaminase (Chapter 6). The conversion of UTP to CTP is catalysed by CTP synthetase.

Scheme 9.1 Multi-step enzymatic process for the production of 2 -deoxyribonucleoside from glucose, acetaldehyde and a nucleobase through the reverse reactions of2 -deoxy-ribonucleoside degradation.

Fig. 7.1.1 Structure of the naturally occurring purine (deoxy)ribonucleosides and nucleoside bases...

Using RNA core as the substrate, EDTA and sulfhydryl reagents are activators Mg2+, Mn2+, and, more effectively, Cu2+, Hg2+, and Zn2+ are inhibitors arsenite and fluoride are weak inhibitors (14) Deoxy-ribonucleoside-3 -phosphates are competitive inhibitors of the activity on acid DNase digests. 

A. Koch, C. Lamberth, F. Wetterich, and B. Giese, Radical rearrangement of 2-0-(di-phenylphosphoryl)glycosyl bromides. A new synthesis for 2-deoxy disaccharides and 2-deoxy ribonucleosides, J. Org. Chem., 58 (1993) 1083-1089. 

Phosphonylation. This reagent is useful for preparation of protected deoxy-ribonucleoside-3-hydrogen phosphonates (2), which can be used for synthesis of deoxyribonucleotides. 

N -(2 -deoxy-ribonucleoside) and the 7-deazaguanine C8-(-2 -deoxyribonucleo-side), compounds (47) and (48), respectively. Compound (47) was obtained from the glycosylation of 8-aza-7-deaza-6-methoxypurine with an appropriately protected a-halogenose while (48) was prepared from the reaction of 7-deazaguanine with l-0-acetyl-2,3,5-tribenzoyl-P-D-ribofuranose in the presence of tin tetra-chloride. ... 

The structure of purine ribonucleosides has recently been studied by proton-magnetic resonance, and the conformation of the D-ribofuranosyl residue in adenosine and inosine has been determined by an analysis of proton-magnetic resonance data C-2 is considered to be out of the plane defined either by C-1, 0, and C-4 or by C-1, 0, C-3, and C-4 and is pointing on the same side as the C-4—C-5 bond. A similar study of deoxy-ribonucleosides suggests that the ring-oxygen atom and, possibly, C-1 of this sugar moiety may be twisted out of the plane of the five-membered... 

Practical synthesis of enantiopure spiro[4.4]nonane C-(2 -deoxy) ribonucleosides was accomplished using a LiBr/Li2CC>3 mediated dehydrobromination of intermediate 31.22... 

Nucleosides prepared conventionally from deoxy-sugars have included the antiviral nucleoside dihydro-5-azathymidine (12), the tritiated analogue (13), and the 6-substituted derivatives (14) (Scheme 2), [ C-2] and [ C-4]-2-deoxy-uridine, and 2-deoxy-ribonucleosides from 5-azapyrimidine derivatives, ... 

A new method for the stereocontrolled synthesis of pyrimidine p-D-2 -deoxy-ribonucleosides involves the use of a photolabile directing group at C-2, and is illustrated by the case in Scheme 2. New glycosyl donors that have been employed with good to excellent stereoselectivity in reactions with silylated pyrimidines are the deoxyribofuranosyl phosphoramidate 36 and the thiocarba-mate 37 in this latter case, intramolecular participation by the sulfur is thought to be involved in ensuring P-selectivity. ... 

Experiments with animal cells have shown that the pyrimidine bases are much less effective DNA precursors than the corresponding deoxy-ribonucleosides, although the interpretation of such experiments is complicated by the rapid catabolism of uracil and thymine which takes place in liver. The incorporation of thymine into DNA in animals (14), or in in vitro systems (15) is slow and contrasts with the much more rapid incorporation of thymidine. 

B. Munch-Petersen, G. Tyrsted and B. Dupont. The deoxy-ribonucleoside-5 -triphosphate (dATP and dTTP pool) in phytohemagglutinin stimulated and non stimulated human l3nnphocytes. 

Since the pyrimidines of RNA as well as those of DNA were labeled after administration of isotopic cytidine, it was suggested that there had lieen a conversion of a pyrimidine ribonucleoside to a pyrimidine deoxy-ribonucleoside (317). It was reasoned that cytidine could not have lieen split to cytosine and then reincorporated into deoxycytidine, because cytosine was not utilized for the synthesis of nucleic acid p3uimidines (303). The suggested conversion may possibly have occurred at the nu cleotide level, thus, cytidylic acid may have been the intermediate in the transformation of RNA to DNA pyrimidines. 

The preparation of the 1,4-anhydroalditol (17) from l-chloro-2-deoxy-3,5-di-p-toluyl-D-gryrtro-pentosyl chloride as part of a programme towards the synthesis of "abasic" 2 -deoxy-ribonucleoside analogues which could readily be turned into the corresponding 5 -(7-dimethoxytrityl-3 -0- 3-cyanoethyl-N,A -di-isopropylamino-phosphoramidate monomers has been reported. These latter compounds can be transformed into homo-oligodeoxy-ribonucleotides and oligodeoxyribonucleotides. ... 

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