Nucleosides and Nucleotides p. 619 - 629 (1996)
Update date:2022-08-16
Topics:
Zemlicka, Jiri
Endo, Takeshi
O6-(4-Nitrophenyl)inosine (1a), O6-(4-nitrophenyl)guanosine (1c) and O6-(4-methylumbelliferonyl)inosine (2) were obtained by reaction of 6-chloro-9-(β-D-ribofuranosyl)purine (3a) or 2-amino-6-chloro-9-(β-D-ribofuranosyl)purine (3c) with sodium salts of 4-nitrophenol or 4-methylumbelliferone in N,N-dimethylformamide. Similarly, 6-chloro-9-(β-D-2,3-isopropylideneribofuranosyl)purine (3b) was transformed to 2',3'-O-isopropylidene-O6-(4-nitrophenyl)inosine (1b). Deprotection of 1b with CF3COOH gave compound 1a and O6-(4-nitrophenyl)hypoxanthine (4). Compounds 1a and 1c are substrates for adenosine deaminase releasing 4-nitrophenol which is readily detected visually or spectrophotometrically. Rate and extent of hydrolysis of 1a are significantly increased in the presence of purine nucleoside phosphorylase but xanthine oxidase has no influence. A potential fluorogenic analogue 2 is not a substrate for adenosine deaminase.
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