O6-(4-nitrophenyl)inosine and -guanosine as chromogenic substrates for adenosine deaminase

Article abstract of DOI:10.1080/07328319608002410

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.

Full text of DOI:10.1080/07328319608002410

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O -(4-Nitrophenyl)inosine and -
Guanosine as Chromogenic Substrates
for Adenosine Deaminase
a
a
Jiri Zemlicka & Takeshi Endo
a
Department of Chemistry, Developmental Therapeutics
Program , Michigan Cancer Foundation, Wayne State University
School of Medicine , Detroit, Michigan, 48201-1379
Published online: 21 Aug 2006.
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To cite this article: Jiri Zemlicka & Takeshi Endo (1996) O -(4-Nitrophenyl)inosine and -Guanosine
as Chromogenic Substrates for Adenosine Deaminase , Nucleosides and Nucleotides, 15:1-3,
619-629
To link to this article: http://dx.doi.org/10.1080/07328319608002410
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