716-17-6

Basic information

• Product Name: (2R)-3-(6-aminopurin-9-yl)propane-1,2-diol
• Synonyms: (2R)-3-(6-aminopurin-9-yl)propane-1,2-diol;9-(2,3-dihydroxypropyl)adenine;1,2-Propanediol, 3-(6-amino-9H-purin-9-yl)-;2,3-Dihydroxypropyladenine;3-(6-Amino-9H-purin-9-yl)-1,2-propanediol
• CAS NO: 716-17-6
• Molecular Formula: C₈H₁₁N₅O₂
• Molecular Weight: 0
• Mol File: 716-17-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 577.8°C at 760 mmHg
• Flash Point: 303.2°C
• Appearance: /
• Density: 1.73g/cm³
• Vapor Pressure: 3.43E-14mmHg at 25°C
• Refractive Index: 1.788
• CAS DataBase Reference: (2R)-3-(6-aminopurin-9-yl)propane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-3-(6-aminopurin-9-yl)propane-1,2-diol(716-17-6)
• EPA Substance Registry System: (2R)-3-(6-aminopurin-9-yl)propane-1,2-diol(716-17-6)

Safety Data

• Hazardous Substances Data: 716-17-6(Hazardous Substances Data)

Usage

Description

(2R)-3-(6-aminopurin-9-yl)propane-1,2-diol is a purine derivative that is structurally related to adenine, a nucleobase present in DNA and RNA. This chemical compound features a purine base with a propylene glycol chain attached, playing a significant role in the structure and function of nucleic acids, which is essential for the storage and transfer of genetic information.

Uses

Used in Biochemistry and Molecular Biology Research:
(2R)-3-(6-aminopurin-9-yl)propane-1,2-diol serves as a research tool in biochemistry and molecular biology, aiding scientists in understanding the mechanisms of nucleic acid function and the role of purines in biological processes.
Used in the Synthesis of Nucleoside Analogs:
(2R)-3-(6-aminopurin-9-yl)propane-1,2-diol is utilized in the synthesis of nucleoside analogs, which are structurally similar to natural nucleosides but differ in specific functional groups. Nucleoside analogs have applications in various fields, including medicine, where they can be used as antiviral or anticancer agents due to their ability to interfere with nucleic acid synthesis and function.

InChI:InChI=1/C8H11N5O2/c9-7-6-8(11-3-10-7)13(4-12-6)1-5(15)2-14/h3-5,14-15H,1-2H2,(H2,9,10,11)

Upstream product

• 69369-04-6 9-(RS)-(2,3-dihydroxypropyl)-8-bromoadenine 
• 4704-77-2 1-bromo-2,3-propanediol 
• 66224-66-6 adenine 
• 94535-32-7 (RS)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid 
• 556-52-5 oxiranyl-methanol 
• 76512-99-7 N⁶-formyl-9-(2,3-dihydroxypropyl)adenine 
• 94535-30-5 Methyl (RS)-3-(Adenin-9-yl)-2-hydroxypropanoate 
• 23485-30-5 N⁹-(2,2-diethoxyethyl)adenine 
• 33841-98-4 2-(6-amino-9H-purin-9-yl)acetaldehyde 

Downstream Products

• 81546-79-4 9-((RS)-3-p-toluenesulfonyloxy-2-(tetrahydropyran-2-yloxy)propyl)adenine 
• 87888-92-4 C₂₂H₂₃N₅O₇S₂ 
• 87888-91-3 Toluene-4-sulfonic acid 3-(6-amino-8-hydroxy-purin-9-yl)-2-hydroxy-propyl ester 
• 123156-39-8 [2-(6-Benzoylamino-purin-9-yl)-1-hydroxy-ethyl]-phosphonic acid diethyl ester 
• 87888-88-8 8-Benzyloxy-9-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-9H-purin-6-ylamine 
• 123156-36-5 2-(N⁶-benzoyladenin-9-yl)ethanal 
• 85446-34-0 9-(RS)-(2,3-dihydroxypropyl)-6-hydroxylaminopurine 
• 69369-04-6 9-(RS)-(2,3-dihydroxypropyl)-8-bromoadenine 
• 70259-40-4 9-((RS)-2,3-bis-p-toluenesulfonyloxypropyl)adenine 

Relevant articles and documents

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

Reaction of 8-Substituted Adenines with Glycidol

The regioselectivity of isomer formation in the reaction of 8-substituted adenines with glycidol depends on steric factors of substituents.The compounds prepared were tested for immunostimulating activity.

EASY ALKYLATION OF PURINE BASES BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT SOLVENT. STRUCTURAL ANALYSIS BY 2D HETERONUCLEAR 1H 13C CORRELATED NMR SPECTROSCOPY

Solid-liquid PTC without added organic solvent promotes alkylation of purine derivatives leading in particular to an efficient synthesis of the antiviral DHPA.The location of the substituent on the ring was determined by analysis of coupling interactions