4546-54-7

Basic information

• Product Name: 2-Aminopurine riboside
• Synonyms: 2-AMINO-9-(BETA-D-RIBOFURANOSYL)PURINE;2-AMINOPURINE RIBOSIDE;2-Amino-9-b-D-ribofuranosylpurine;2-(2-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;2-Amino-9-beta-D-ribofuranosyl-9H-purine;2-Amino-9--D-ribofuranosylpurine;2-(2-aminopurin-9-yl)-5-methylol-tetrahydrofuran-3,4-diol;2-(2-azanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS NO: 4546-54-7
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24
• EINECS: 1312995-182-4
• Product Categories: Bases & Related Reagents;Nucleotides;Amines
• Mol File: 4546-54-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 105-115°C
• Boiling Point: 711.8oC at 760 mmHg
• Flash Point: 384.3oC
• Appearance: Off-white crystalline solid
• Density: 2.08 g/cm3
• Vapor Pressure: 2.88E-21mmHg at 25°C
• Refractive Index: 1.907
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• CAS DataBase Reference: 2-Aminopurine riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminopurine riboside(4546-54-7)
• EPA Substance Registry System: 2-Aminopurine riboside(4546-54-7)

Safety Data

• Hazardous Substances Data: 4546-54-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Crystalline Solid

Uses

2-Aminopurine Riboside is a probe of structural dynamics and charge transfer in DNA. Potential activator or inhibitor of B. anthracis spore germination.

InChI:InChI=1/C10H13N5O4/c11-10-12-1-4-8(14-10)15(3-13-4)9-7(18)6(17)5(2-16)19-9/h1,3,5-7,9,16-18H,2H2,(H2,11,12,14)

Upstream product

• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 118-00-3 G 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 30747-23-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 190773-85-4 9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-6-chloro-9H-purin-2-ylamine 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 452-06-2 9H-purin-2-amine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 1053614-74-6 9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-ylamine 
• 85-31-4 6-mercaptoguanosine 
• 107037-21-8 2-amino-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 100122-98-3 2-benzoylamidopurine 

Downstream Products

• 129944-21-4 N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 129944-20-3 N²-benzoyl-9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purin-2-amine 
• 129944-19-0 N-benzoyl-9-[5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-ribofuranosyl]-9H-purin-2-amine 
• 107037-23-0 2-Iodo-9-<2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>purine 
• 107037-30-9 3-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-[(Z)-3-hydroxy-but-2-en-(E)-ylidene]-3,5-dihydro-imidazol-(4E)-ylidene-cyanamide 
• 107037-22-9 2',3',5'-tri-O-tert-butyldimethylsilyl-9-(β-D-ribofuranosyl)-2-amino-purine 
• 129944-18-9 N-benzoyl-9-(β-D-ribofuranosyl)-9H-purin-2-amine 

Relevant articles and documents

Practical synthesis of N-(di-n-butylamino)methylene-protected 2-aminopurine riboside phosphoramidite for RNA solid-phase synthesis

2-Aminopurine (Ap) is a fluorescent nucleobase analog that is frequently used as structure-sensitive reporter to study the chemical and biophysical properties of nucleic acids. In particular, thermodynamics and kinetics of RNA folding and RNA–ligand binding, as well as RNA catalytic activity are addressable by pursuing the Ap fluorescence signal in response to external stimuli. Site-specific incorporation of Ap into RNA is usually achieved by RNA solid-phase synthesis and requires appropriately functionalized Ap riboside building blocks. Here, we introduce a robust synthetic path toward a 2-aminopurine riboside phosphoramidite whose N2 functionality is masked with the N-(di-n-butylamino)methylene group. This protection is considered advantageous over previously described N-(dimethylamino)methylene or acyl protection patterns needed for the fine-tuned deprotection conditions to achieve large synthetic RNAs. Graphic abstract: [Figure not available: see fulltext.].

Efficient removal of sugar O-tosyl groups and heterocycle halogens from purine nucleosides with sodium naphthalenide

Sodium naphthalenide effects removal of 2'-, 3'-, or 5'-O-tosyl groups from the sugar, and 2-, 6-, or 8-halogens from purine nucleosidcs. An improved tosyl protection strategy was developed for the synthesis of 9-(3-deoxy-3-fluoro-β-D-xylofuranosyl)adenine from 2',5'-di-O-tosyladenosine.

Chemical Synthesis of Oligoribonucleotides Containing 2-Aminopurine: Substrates for the Investigation of Ribozyme Function

The chemical synthesis of a fully protected ribonucleoside phosphoramidite, containing 2-aminopurine as the base component, and its incorporation into short oligoribonucleotides as substrate for an engineered riboenzyme from Tetrahymena is described.