444989-19-9

Upstream product

• 444989-16-6 8-bromo-N¹-[(2-acetoxyethoxy)-methyl]-5'-O-dianilinophosphoryl-2',3'-O-isopropylideneinosine 
• 444989-14-4 8-bromo-N¹-[(2-acetoxyethoxy)-methyl]-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneinosine 
• 203249-43-8 5'-O-TBDMS-2',3'-O-isopropylidene-8-bromoinosine 
• 444989-18-8 8-chloro-N¹-[[[bis(phenylthio)phosphoryl]oxy-ethoxy]methyl]-5'-O-(dianilinophosphoryl)-2',3'-O-isopropylideneinosine 

Relevant academic research and scientific papers

Syntheses and calcium-mobilizing evaluations of N1-glycosyl-substituted stable mimics of cyclic ADP-ribose

Cyclic ADP-ribose (cADPR) is not only a potent endogenous calcium modulator but also a second messenger. However, studies on the mechanism of cADPR action were limited due to its instability and lack of available structural modifications in the N1-glyosyl unit of cADPR. In the present work, a series of N1-glycosyl mimics with different configurational glycosyls or an ether strand were designed and synthesized mimicking the furanose ring. SN2 substitutions were carried out between the protected inosine and glycosyl triflates to form the N1-glycosylinosine derivatives, accompanied with some O6-glycosyl-substituted as side products. The intramolecular cyclization was followed the strategy described by Matsuda et al. It was found that the 8-unsubstituted substrate could also be used to construct the intramolecular cyclic pyrophosphate. The activities of N1-glycosyl-substituted cADPR mimics were evaluated by induced Ca2+ release in rat brain microsomes and HeLa cells. It was found that the configuration of the N1-glycosyl moiety in cADPR is not a critical structural factor for retaining the activity of mobilizing Ca2+ release. More interestingly, the N1-acyclic analogue 6 exhibited strong activity by inducing Ca2+ release in both rat brain microsomes and HeLa cells. It constitutes a useful tool for further studies.

Chemical synthesis and calcium release activity of N1-ether strand substituted cADPR mimic

8-Chloro cyclic inosine 5′-diphosphate ethoxymethyl ether 3 was synthesized by means of chemical method from protected inosine via phenylthio-type biphosphate substrate. The detection of Ca2+ release activity shows that 3 is a potent agonist of cADPR and has activity in intact Hela cells.