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C-Glycosylphosphonyl Analogs of 5-Phosphorylribose 1-α-Diphosphate: II. The “2-Deoxy” Analog

✍ Scribed by John F. Witte; Ronald W. McClard

Book ID: 102563837
Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 178 KB
Volume: 24
Category: Article
ISSN: 0045-2068
DOI: 10.1006/bioo.1996.0004

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✦ Synopsis

D-ribo-2,5-anhydro-1,3-dideoxy-1-(((dihydroxyphosphinyl)oxy)hydroxyphosphinyl)-6-phosphorylhexitol, compound 4, along with 25% of its D-arabino epimer, was synthesized in 10 steps from 2-deoxyribonolactone. Compound 4 represents the 2-deoxy analog of the central metabolite 5-phosphorylribose 1-Ͱ-diphosphate (PRPP). The analog is a competitive inhibitor of yeast orotate phosphoribosyltransferase (PRTase) with K i /K m(PRPP) ϭ 24 and is thus comparable to other C-glycosylphosphonyl PRPP analogs reported previously (R. W. McClard, and J. F. Witte (1990) Bioorg. Chem. 18, 165-178). The analog is an even better inhibitor of both human hypoxanthine-guanine PRTase and glutamine : amido PRTase from Escherichia coli with K i /K m(PRPP) values of 16 and 3, respectively. These results support the argument that the cis-diol grouping of nucleotides (or PRPP) plays a very minor role in binding of these substrates to PRTases.

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