ChemInform Abstract: Synthesis of Nucleosides and Related Compounds. Part 42. Deamination of Cyclaradine by Adenosine Deaminase under High Pressure.

ChemInform ◽  
2010 ◽  
Vol 29 (28) ◽  
pp. no-no
Author(s):  
N. KATAGIRI ◽  
H. KOKUFUDA ◽  
M. MAKINO ◽  
R. VINCE ◽  
C. KANEKO
Keyword(s):  
High Pressure ◽  
Adenosine Deaminase ◽  
Related Compounds

scholarly journals Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase

1973 ◽  
Vol 51 (19) ◽  
pp. 3161-3169 ◽  
Author(s):  
Morris J. Robins ◽  
Gerald L. Basom
Keyword(s):  
Adenosine Deaminase ◽  
Methylene Chloride ◽  
Potassium Fluoride ◽  
Direct Conversion ◽  
Chloride Complex ◽  
High Yield ◽  
Mass Spectral ◽  
Quaternary Ammonium Chloride ◽  
Related Compounds

Trifluoroacetylation of 2′-deoxyinosine (2), obtained by enzymatic deamination of 2′-deoxyadenosine (1), gave the 3′,5′-bis-O-trifluoroacetate (3). Reaction of the electronegatively substituted deoxynucleoside, 3, with DMF-thionyl chloride complex in refluxing methylene chloride gave a high yield of 6-chloropurine 2′-deoxyriboside (4) after deblocking.Displacement of chloride of 4 by hydrosulfide to give 6-mercaptopurine 2′-deoxyriboside (5) followed by sulfur alkylation with p-nitrobenzyl bromide gave 6-S-(p-nitrobenzyl) thiopurine 2′-deoxyriboside (6) which was alternatively prepared by displacement of chloride from 4 by p-nitrobenzyl mercaptide, generated in situ from the isothiouronium salt. Methyl mercaptide reaction with 4 gave 6-methylthiopurine 2′-deoxyriboside (7). Treatment of 4 with trimethylamine gave the corresponding quaternary ammonium chloride (8) which was allowed to react with potassium fluoride to give 6-fluoropurine 2′-deoxyriboside (9). Respective amine displacements on 4 gave 6-benzylaminopurine 2'-deoxyriboside (10), and 6-hydroxylaminopurine 2′-deoxyriboside (11). Reaction of 4 with liquid ammonia completed the first reported transformation of 2′-deoxyinosine (2) to 2′-deoxyadenosine (1).Biological rationale for the synthesis of these 2′-deoxynucleosides and their evaluation as substrates of adenosine deaminase are discussed. Major mass spectral fragmentations are tabulated.

Sign in / Sign up

Export Citation Format

Share Document