7403-25-0

Basic information

• Product Name: 3'-Amino-2',3'-dideoxyadenosine
• Synonyms: 3'-AMINO-2',3'-DEOXY-D-ADENOSINE;3'-AMINO-2',3'-DIDEOXYADENOSINE;3'-AMINO-2'-DEOXY-D- ADENOSINE;3'-Amino-2',3'-dideoxy-D-adenosine;2',3'-dideoxy-3'-aminoadenosine;[(2S,3S,5R)-3-Amino-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol;9-(3-Amino-2,3-dideoxy-β-D-ribofuranosyl)hypoxanthine;3'-NH2-ddA
• CAS NO: 7403-25-0
• Molecular Formula: C₁₀H₁₄N₆O₂
• Molecular Weight: 250.26
• Mol File: 7403-25-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 571.6 °C at 760 mmHg
• Flash Point: 299.5 °C
• Appearance: Off-white to Yellow/Powder
• Density: 1.91 g/cm³
• CAS DataBase Reference: 3'-Amino-2',3'-dideoxyadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Amino-2',3'-dideoxyadenosine(7403-25-0)
• EPA Substance Registry System: 3'-Amino-2',3'-dideoxyadenosine(7403-25-0)

Safety Data

• Hazardous Substances Data: 7403-25-0(Hazardous Substances Data)

Usage

General Description

3'-Amino-2',3'-dideoxyadenosine is a chemical compound that belongs to the class of adenosine analogs. It is a modified form of the nucleoside adenosine, where a hydroxyl group at the 3' position of the sugar ring is replaced by an amino group and the 2' and 3' hydroxyl groups are removed. This modification makes the molecule resistant to degradation by adenosine deaminase, an enzyme that normally metabolizes adenosine in the body. 3'-Amino-2',3'-dideoxyadenosine has been studied for its potential medical applications, including as an anti-viral agent and as a potential treatment for certain types of cancers. It has also been investigated for its ability to inhibit DNA replication in viruses, making it a potential candidate for antiviral drug development.

Upstream product

• 66323-44-2 9-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine 
• 66224-66-6 adenine 
• 52450-18-7 3'-amino-3'-deoxythymidine 
• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 

Downstream Products

• 899435-22-4 3'-tritylamino-2',3'-dideoxyadenosine 
• 195375-63-4 N-benzoyl-2 ^{FontWeight=Bold FontSize=10} ',3'-dideoxy-3'-[(triphenylmethyl)amino]adenosine 
• 1345543-68-1 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-oxo-3-(pentafluorophenyloxy)propyl]}glutaryl-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine 
• 1417713-27-9 C₃₅H₄₂N₆O₂Si 
• 195375-62-3 N-{9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 
• 1417713-29-1 (1'R, 3'S, 4'S)-2',3'-dideoxy-3'-tritylamino-N⁶-benzoyl-adenin-4'-carboxylic acid 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 

Relevant articles and documents

Chemical-enzymatic synthesis of 3'-amino-2',3'-dideoxy-β-D- ribofuranosides of natural heterocyclic bases and their 5'-monophosphates

Treatment of O2,3'-anhydro-5'-O-trityl derivatives of thymidine (1) and 2'-deoxyuridine (2) with lithium azide in dimethylformamide at 150 °C resulted in the formation of the corresponding isomeric 3'-azido-2',3'- dideoxy-5'-O-trityl-β-D-ribofuranosyl N1- (the major products) and N3- nucleosides 3/4 and 5/6). 3'-Amino-2',3'-dideoxy-β-D-ribofuranosides of thymidine [Thd(3'NH2)], uridine [dUrd(3'NH2)], and cytidine [dCyd(3'NH2)] were synthesized from the corresponding 3'-azido derivatives. The Thd(3'NH2) and dUrd(3'NH2) were used as donors of carbohydrate moiety in the reaction of enzymatic transglycosylation of adenine and guanine to afford dAdo(3'NH2) and dGuo(3'NH2). The substrate activity of dN(3'NH2) vs. nucleoside phosphotransferase of the whole cells of Erwinia herbicola was studied.