58328-93-1

Upstream product

• 5843-59-4 6-chloropurine riboside 5'-monophosphate 
• 97-55-2 5-phosphoribosyl-1-pyrophosphate 
• 50-44-2 6-mercaptopurine 
• 60095-36-5 2',3'-O-isopropylidene-6-thioinosine 
• 574-25-4 6-thioinosine 
• 1359697-38-3 2',3'-O-isopropylidene-6-(2,4-dinitrophenyl)thioinosine 
• 1375103-71-1 2',3'-O-isopropylidene-5'-O-(di-tert-butylphosphoramidite)-6-thioinosine 
• 1359697-42-9 2',3'-O-isopropylidene-5'-O-(di-tert-butylphosphoramidite)-6-(2,4-dinitrophenyl)thioinosine 
• 50-44-2 6H-purine-6-thione 
• 532-20-7 D-Ribose 
• 2004-06-0 6-Chloropurine riboside 
• 78681-85-3 Phosphoric acid (3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester bis-(2,2,2-tribromo-ethyl) ester 
• 39824-26-5 6-chloro-9-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine 

Relevant academic research and scientific papers

Aberrant cyclization affords a C-6 modified cyclic adenosine 5′-diphosphoribose analogue with biological activity in Jurkat T cells

Two nicotinamide adenine dinucleotide (NAD+) analogues modified at the 6 position of the purine ring were synthesized, and their substrate properties toward Aplysia californica ADP-ribosyl cyclase were investigated. 6-N-Methyl NAD+ (6-N-methyl nicotinamide adenosine 5′-dinucleotide 10) hydrolyzes to give the linear 6-N-methyl ADPR (adenosine 5′-diphosphoribose, 11), whereas 6-thio NHD+ (nicotinamide 6-mercaptopurine 5′-dinucleotide, 17) generates a cyclic dinucleotide. Surprisingly, NMR correlation spectra confirm this compound to be the N1 cyclic product 6-thio N1-cIDPR (6-thio cyclic inosine 5′-diphosphoribose, 3), although the corresponding 6-oxo analogue is well-known to cyclize at N7. In Jurkat T cells, unlike the parent cyclic inosine 5′-diphosphoribose N1-cIDPR 2, 6-thio N1-cIDPR antagonizes both cADPR- and N1-cIDPR-induced Ca2+ release but possesses weak agonist activity at higher concentration. 3 is thus identified as the first C-6 modified cADPR (cyclic adenosine 5′-diphosphoribose) analogue antagonist; it represents the first example of a fluorescent N1-cyclized cADPR analogue and is a new pharmacological tool for intervention in the cADPR pathway of cellular signaling.

Five-component cascade synthesis of nucleotide analogues in an engineered self-immobilized enzyme aggregate

(Chemical Equation Presented) Pathway in a particle: A five-enzyme biosynthetic pathway was self-immobilized to form a single biocatalyst for generation of purine nucleotide analogues from d-ribose. This method provides an alternative to engineering biosynthetic pathways in whole cells that obviates problems associated with toxicity, transport and genetic regulation.