25030-19-7

Basic information

• Product Name: 2-amino-9-[5-deoxy-2,3-O-(1-methylethylidene)-5-triaza-1,2-dien-2-ium-1-ylpentofuranosyl]-3,9-dihydro-6H-purin-6-one
• CAS NO: 25030-19-7
• Molecular Formula: C₁₃H₁₆N₈O₄
• Molecular Weight: 349.3247
• Mol File: 25030-19-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-amino-9-[5-deoxy-2,3-O-(1-methylethylidene)-5-triaza-1,2-dien-2-ium-1-ylpentofuranosyl]-3,9-dihydro-6H-purin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-9-[5-deoxy-2,3-O-(1-methylethylidene)-5-triaza-1,2-dien-2-ium-1-ylpentofuranosyl]-3,9-dihydro-6H-purin-6-one(25030-19-7)
• EPA Substance Registry System: 2-amino-9-[5-deoxy-2,3-O-(1-methylethylidene)-5-triaza-1,2-dien-2-ium-1-ylpentofuranosyl]-3,9-dihydro-6H-purin-6-one(25030-19-7)

Safety Data

• Hazardous Substances Data: 25030-19-7(Hazardous Substances Data)

Usage

Chemical compound

2-amino-9-[5-deoxy-2,3-O-(1-methylethylidene)-5-triaza-1,2-dien-2-ium-1-ylpentofuranosyl]-3,9-dihydro-6H-purin-6-one

Structure

Complex molecule with a purine base structure

Functional groups

Amino group at position 2, pentofuranose ring linked to position 9, triaza-diene-ium moiety attached to the pentofuranose ring

Derivative of

Adenine

Biological activity

Potential due to structural similarity to adenine and its derivatives

Potential applications

Pharmacological or therapeutic properties

Upstream product

• 39947-13-2 5'-O-tosyl-2',3'-O-isopropylideneguanosine 
• 362-76-5 2',3'-isopropylideneguanosine 

Relevant articles and documents

Synthesis of Triazole-Linked Analogues of c-di-GMP and Their Interactions with Diguanylate Cyclase

Cyclic di-GMP (c-di-GMP) is a widespread second messenger that plays a key role in bacterial biofilm formation. The compound's ability to assume multiple conformations allows it to interact with a diverse set of target macromolecules. Here, we analyzed the binding mode of c-di-GMP to the allosteric inhibitory site (I-site) of diguanylate cyclases (DGCs) and compared it to the conformation adopted in the catalytic site of the EAL phosphodiesterases (PDEs). An array of novel molecules has been designed and synthesized by simplifying the native c-di-GMP structure and replacing the charged phosphodiester backbone with an isosteric nonhydrolyzable 1,2,3-triazole moiety. We developed the first neutral small molecule able to selectively target DGCs discriminating between the I-site of DGCs and the active site of PDEs; this molecule represents a novel tool for mechanistic studies, particularly on those proteins bearing both DGC and PDE modules, and for future optimization studies to target DGCs in vivo.

A general synthesis of 5′-azido-5′-2′,3′-O-isopropylidene nucleosides

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