1146899-09-3

Basic information

• Product Name: 6-amino-5',2,6-tri-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-3'-O-(α-D-glucopyranosyl)-9-β-D-ribofuranosylpurine
• Synonyms: 6-amino-5',2,6-tri-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-3'-O-(α-D-glucopyranosyl)-9-β-D-ribofuranosylpurine
• CAS NO: 1146899-09-3
• Molecular Weight: 1220.22
• Mol File: 1146899-09-3.mol

Chemical Properties

• CAS DataBase Reference: 6-amino-5',2,6-tri-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-3'-O-(α-D-glucopyranosyl)-9-β-D-ribofuranosylpurine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-5',2,6-tri-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-3'-O-(α-D-glucopyranosyl)-9-β-D-ribofuranosylpurine(1146899-09-3)
• EPA Substance Registry System: 6-amino-5',2,6-tri-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-3'-O-(α-D-glucopyranosyl)-9-β-D-ribofuranosylpurine(1146899-09-3)

Safety Data

• Hazardous Substances Data: 1146899-09-3(Hazardous Substances Data)

Relevant articles and documents

Contribution of phosphates and adenine to the potency of adenophostins at the IP3 receptor: Synthesis of all possible bisphosphates of adenophostin A

Although adenophostin A (AdA), the most potent agonist of d-myo-inositol 1,4,5-trisphosphate receptors (IP3R), is thought to mimic IP 3, the relative roles of the different phosphate groups and the adenosine motif have not been established. We synthesized all three possible bisphosphate analogues of AdA and glucose 3,4-bisphosphate (7, AdA lacking the 2′-AMP). 2′-Dephospho-AdA (6) was prepared via a novel regioselective dephosphorylation strategy. Assessment of the abilities of these bisphosphates to stimulate intracellular Ca2+ release using recombinant rat type 1 IP3R (IP3R1) revealed that 6, a mimic of Ins(4,5)P2, is only 4-fold less potent than IP3, while 7 is some 400-fold weaker and even 3′3-dephospho-AdA (5) is measurably active, despite missing one of the vicinal bisphosphate groups normally thought to be crucial for IP3-like activity. Compound 6 is the most potent bisphosphate yet discovered with activity at IP3R. Thus, adenosine has a direct role independent of the 2′-phosphate group in contributing toward the potency of adenophostins, the vicinal bisphosphate motif is not essential for activity at the IP3R, as always thought, and it is possible to design potent agonists with just two of the three phosphates. A model with a possible adenine-R504 interaction supports the activity of 5 and 6 and also allows a reappraisal of the unexpected activity previously reported for the AdA regioisomer 2′3-phospho-3′3- dephospho-AdA 40.

Activation of IP3 receptors by synthetic bisphosphate ligands

Ca2+ release by d-myo-inositol 1,4,5-trisphosphate receptors (IP3Rs) is widely considered to require the vicinal 4,5-bisphosphate motif of IP3, with P-5 and P-4 engaging the α and β domains of the binding site; using synth