Studies on Synthetic Nucleotides. IV. Preparation of L-β-Ribonucleosides and L-β-Ribonucleotides.

L‐[3H]Adenosine, a New Metabolically Stable Enantiomeric Probe for Adenosine Transport Systems in Rat Brain Synaptoneurosomes

“…In the present study L-adenosine was not found to be metabolized by rat brain AK or ADA. Biologically, D-adenosine, but not L-adenosine, was able to support the growth of mammalian cells in culture (Asai et al, 1967). In addition, L-enantiomers of adenosine, AMP, ADP, ATP, and 5'-(N-ethylcarboxamido)adenosine were found to be inactive at pharmacologically relevant concentrations in tests of human platelet aggregation (Cusack et al, 1979;Cusack and Hourani, 198 1) and relaxation of guinea pig taenia coli (Cusack and Planker, 1979).…”

“…L-Adenosine and other L-ribose-substituted nucleobases were first synthesized starting in 1964 with the intention that new, more metabolically stable analogs might be identified that would facilitate the study of nucleic acids and increase the therapeutic usefulness of nucleosides such as 6-mercaptopurine (Acton et al, 1964). Metabolically, the L-isomer of adenosine was found not to be metabolized by ADA from Aspergillus oryzae, nor was the L-isomer of 5'-AMP dephosphor-ylated by 5'-nucleotidase from Trimeresurus Jlavoviridis (Asai et al, 1967). In the present study L-adenosine was not found to be metabolized by rat brain AK or ADA.…”

The use of protecting groups in the synthesis of purine derivatives (review)

“…Hydrolysis of these esters by the action of phosphodiesterase in a buffer solution at pH 9 led to the production of 9-β-D-ribofuranosyl 5'-phosphates of adenine (5'-AMP) and hypoxanthine 175 (IMP). The yields of compounds 172-175 amounted to 38-59, 97, 88, and 39-42% respectively [99][100][101]. …”

“…With silyl protection it is possible to produce nucleotides by the condensation of silylpurines with phosphoryl derivatives of sugars. Thus, the fusion of silylpurines 156 with 5-diphenylphosphoryl-2,3-di-O-benzoyl-D-ribofuranosyl bromide at 100-110°C gave 9-substituted silylpurines 171 [99,100]. Treatment of the products with aqueous ethanol and then with NaOH in aqueous dioxane and with sodium methoxide in methanol gave compounds 174.…”

Advances in the Synthesis of 7-Deazapurine - Pyrrolo[2,3-d]pyrimidine 2-Deoxyribonucleosides Including D- and L-Enantiomers, Fluoro Derivatives and 2,3-Dideoxyribonucleosides

“…The first L- nucleoside ( -L-dT) was synthesized by mejkal and orm in 1964 [38]; in the same year Acton, Ryan, and Goodman described -L-adenosine [153]. Related ribonucleosides were reported by Shimizu in 1967 [154] and by Hol and orm in 1969 [155]. The discovery of the antiviral activity of 3TC, which is more active and less toxic than its D-counterpart, attracted considerable interest in the synthesis and the pharmacological activity of L-nucleosides [156][157][158][159][160][161][162].…”