Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

ChemInform ◽  
2005 ◽  
Vol 36 (29) ◽  
Author(s):  
Enzo Santaniello ◽  
Pierangela Ciuffreda ◽  
Laura Alessandrini
Keyword(s):  
Adenosine Deaminase ◽  
Adenylate Deaminase ◽  
Related Compounds

Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

Synthesis ◽  
2005 ◽  
Vol 2005 (04) ◽  
pp. 509-526 ◽  
Author(s):  
Enzo Santaniello ◽  
Pierangela Ciuffreda ◽  
Laura Alessandrini
Keyword(s):  
Adenosine Deaminase ◽  
Adenylate Deaminase ◽  
Related Compounds

Phosphorylation of Coformycin and 2′ -Deoxycoformycin, and Substrate and Inhibitor Properties of the Nucleosides and Nucleotides in Several Enzyme Systems

1985 ◽  
Vol 40 (9-10) ◽  
pp. 710-714 ◽  
Author(s):  
Agnieszka Bzowska ◽  
Piotr Lassota ◽  
David Shugara
Keyword(s):  
Nmr Spectroscopy ◽  
Adenosine Deaminase ◽  
Snake Venom ◽  
Purine Nucleoside Phosphorylase ◽  
H Nmr ◽  
Enzyme Systems ◽  
Adenylate Deaminase ◽  
Wheat Shoot ◽  
Neutral Media ◽  
Biological Aspects

Abstract Under conditions where 2′-deoxycoformycin is enzymatically phosphorylated by wheat shoot phosphotransferase to the 5′-phosphate in 15 - 20% yield, coformycin is a relatively poor substrate, and is phosphorylated only to the extent of ≤ 5%. However, chemical phosphorylation of coformycin by modifications of the Yoshikawa procedure led to isolation of coformycin-5′-phosphate in 20% overall yield. Coformycin-5′-phosphate was characterized by various criteria, including 1H NMR spectroscopy. Comparison of the spectrum with that of the parent nucleoside indicated that the nucleotide is predominantly, although not exclusively, in the conformation anti about the glycosidic bond. Like 2′-deoxycoformycin-5′-phosphate, coformycin-5′-phosphate was a feeble substrate of snake venom 5′-nucleotidase, and is hydrolyzed, quantitatively, at only 2% the rate for 5′-AMP. With 5′-AMP analogues as substrate, the 5′-phosphates of both coformycin and deoxycoformycin were poor inhibitors of the enzyme, with Ki values > 0.3 mᴍ. The 5′-phosphates of both coformycin and deoxycoformycin do not significantly inhibit adenosine deaminase (Ki > 0.2 mᴍ), but are potent inhibitors of adenylate deaminase {Ki ≤ 10−9 ᴍ). Neither coformycin nor deoxycoformycin are inhibitors of mammalian purine nucleoside phosphorylase. The stabilities of coformycin, deoxycoformycin, and their 5′-phosphates, have been examined as a function of pH, and nature of the buffer medium. In particular, all exhibit instability in acid and neutral media, but are relatively stable in the vicinity of pH 9. Some biological aspects of the overall results are presented.

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.

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
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