176246-90-5

Upstream product

• 106183-57-7 5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Relevant academic research and scientific papers

C-glycosylphosphonyl analogs of 5-phosphorylribose 1-α-diphosphate: II. The "2-deoxy" analog

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-α-diphosphate (PRPP). The analog is a competitive inhibitor of yeast orotate phosphoribosyltransferase (PRTase) with Ki/Km(PRPP) = 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 Ki/Km(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.