3616-24-8

Usage

Uses

Used in Biophysical Research:
2-AMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE is used as a fluorescent probe for studying nucleic acid structure, dynamics, and interactions. Its intersystem crossing property allows for the investigation of excited-state processes and energy transfer mechanisms in biological systems.
Used in Fluorescence Spectroscopy:
In fluorescence spectroscopy, 2-AMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE serves as a sensitive and versatile reporter molecule. Its fluorescence properties enable the monitoring of molecular interactions, conformational changes, and environmental effects on nucleic acids.
Used in Single-Molecule Studies:
2-AMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE is employed as a fluorescent label in single-molecule experiments, providing insights into the behavior of individual nucleic acid molecules and their interactions with proteins or other ligands.
Used in Bioimaging:
2-AMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE is utilized as a fluorescent tag in bioimaging techniques, such as fluorescence microscopy, to visualize and track nucleic acid molecules within cells and tissues.
Used in Drug Discovery:
In the pharmaceutical industry, 2-AMINO-9-(BETA-D-2-DEOXYRIBOFURANOSYL)PURINE is used as a molecular tool to study the binding and activity of potential drug candidates targeting nucleic acid-based therapeutics. Its fluorescence properties aid in the development of high-throughput screening assays for drug discovery.

InChI:InChI=1/C10H13N5O3/c11-10-12-2-5-9(14-10)15(4-13-5)8-1-6(17)7(3-16)18-8/h2,4,6-8,16-17H,1,3H2,(H2,11,12,14)

Upstream product

• 789-61-7 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-mercapto-9H-purine 
• 961-07-9 2'-Deoxyguanosine 
• 452-06-2 9H-purin-2-amine 
• 951-77-9 2'-Deoxycytidine 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 170872-60-3 Thiocarbonic acid O-[(2R,3R,3aR,9aR)-2-(2-amino-6-chloro-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl] ester O-phenyl ester 
• 87791-91-1 2-amino-6-chloro-9-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]purine 
• 170872-61-4 9-((2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-ylamine 

Downstream Products

• 18620-60-5 2,4-diamino-5-formamidopyrimidine 
• 452-06-2 9H-purin-2-amine 

Relevant academic research and scientific papers

Synthesis of 9-(2-deoxy-β-D-ribofuranosyl)purine-2-thione

A synthesis of 9-(2-deoxy-β-D-ribofuranosyl)purine-2-thione was performed by desulfurization of 2'-deoxy-6-thioguanine to give 2-amino-9-(2- deoxy-β-D-ribofuranosyl)purine, diazotization with chloride replacement to give 2-chloro-9-(2-deoxy-β-D-ribofuranosyl)purine, and the replacement of chloride with sulfur using thiolacetic acid and deacetylation.

One-flask syntheses of 6-thioguanosine and 27′-deoxy-6-thioguanosine

We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2′deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.

A new approach to the synthesis of 2-aminopurine-2'-deoxyriboside via tri- n-butyltin hydride reduction

A simple conversion of guanosine to 2-aminopurine-2'-deoxyriboside is described. Following the synthesis of the 2'-phenoxythiocarbonyl derivative of 6-chloroguanosine, 2-aminopurine-2'-deoxyriboside can be prepared by simultaneous reduction of both the 6-

Chemical and enzymatic synthesis of 2'-deoxy-iso-inosine and its incorporation into DNA

Two procedures for the preparation of 2'-deoxy-iso-inosine (1) are presented. Synthesis of 3'-phosphoramidite (7) and 3'-phosphonate (8) derivatives are described, as well as an oligodeoxynucleotide containing iso-I.

2'-Deoxyisoinosine: Synthesis of a highly fluorescent nucleoside and its incorporation into oligonucleotides

The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'- dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.

Antiviral agents

Nucleoside compounds of the formula STR1 wherein: B is a purine or a pyrimidine; X and X' are H, OH or F, provided that at least one is H; Y and Y' are H, OH, OCH3 or F, provided that at least one is H; Y' and Z together form a cyclic phosphate ester, provided that Y is H; or Z is STR2 where n is zero, one, two or three; and Z' is N3 or OCH3 ; provided that when X' and Y' are OH and Z' is N3, B is not cytosine, and when X' and Y' are OH and Z' is OCH3, B is not uracil, adenine or cytosine; and the pharmaceutically acceptable esters, ethers and salts thereof, have been found to have potent antiviral activity with a high therapeutic ratio.