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Abstract
O6-(4-Nitrophenyl)inosine (la), 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 la and O6 -(4-nitrophenyl)hypoxanthine (4). Compounds 1a and 1c are substrates for adenosine deaminase releasing 4-nitrophenol which is readily detected visually or spectrophotomemcally. Rate and extent of hydrolysis of la 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.
1. For a preliminary report see: Zemlicka, J. in Nucleic Acid Chemistry: Improved and New Synrheric Procedures, Methods and Techniques (Townsend, L. B.; Tipson, R. S., Eds.), Part 4, 1991, Wiley-Interscience, New York, p. 260.
Dedicated to Professor Yoshihisa Mizuno on the occassion of his 75th birthday.
Notes
1. For a preliminary report see: Zemlicka, J. in Nucleic Acid Chemistry: Improved and New Synrheric Procedures, Methods and Techniques (Townsend, L. B.; Tipson, R. S., Eds.), Part 4, 1991, Wiley-Interscience, New York, p. 260.
Dedicated to Professor Yoshihisa Mizuno on the occassion of his 75th birthday.