132628-16-1

Basic information

• Product Name: N2-Phenylacetyl guanosine
• Synonyms: N2-PHENYLACETYL RIBONUCLEOSIDE GUANOSINE;N-(Phenylacetyl)guanosine;N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenylacetaMide;N2-Phenylacetyl guanosine N-(9-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxyMethyl)-tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenylacetaMide;N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-pur;N2-Phenylacetyl Gr;Phenylacetylguanosine;N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-
• CAS NO: 132628-16-1
• Molecular Formula: C₁₈H₁₉N₅O₆
• Molecular Weight: 401.38
• EINECS: 1312995-182-4
• Mol File: 132628-16-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 189℃
• Appearance: /
• Density: 1.73
• Refractive Index: 1.784
• Storage Temp.: 2-8°C
• PKA: 8.80±0.20(Predicted)
• CAS DataBase Reference: N2-Phenylacetyl guanosine(CAS DataBase Reference)
• NIST Chemistry Reference: N2-Phenylacetyl guanosine(132628-16-1)
• EPA Substance Registry System: N2-Phenylacetyl guanosine(132628-16-1)

Safety Data

• Hazardous Substances Data: 132628-16-1(Hazardous Substances Data)

Usage

Description

N2-Phenylacetyl guanosine is a modified nucleoside derivative of guanosine, characterized by the attachment of a phenylacetyl group to the nitrogen-2 position of the guanine base. This chemical modification confers enhanced stability and selectivity to the compound, positioning it as a valuable asset in nucleic acid research and as a prospective therapeutic agent.

Uses

Used in Pharmaceutical Research:
N2-Phenylacetyl guanosine is utilized as a research tool for its potential to inhibit viral replication, making it a candidate for the development of antiviral therapies. Its ability to interfere with the life cycle of viruses could lead to the creation of new treatments for viral infections.
Used in Anticancer Applications:
In the field of oncology, N2-Phenylacetyl guanosine is employed as an anti-cancer agent, demonstrating promising results in preclinical studies. Its potential to target and disrupt cancer cell processes could contribute to the development of novel cancer therapies.
Used in Nucleoside Analog Development:
N2-Phenylacetyl guanosine is used as a starting point for the development of nucleoside analogs for RNA and DNA modification. This application is crucial for the advancement of nucleic acid-based technologies, potentially leading to innovative approaches in genetic research and gene therapy.
Used in Biochemical and Molecular Biology Research:
As a modified nucleoside, N2-Phenylacetyl guanosine is used in biochemical and molecular biology research to study the interactions of nucleic acids with proteins and other biomolecules, providing insights into the fundamental mechanisms of genetic information processing.

InChI:InChI=1/C18H19N5O6/c24-7-10-13(26)14(27)17(29-10)23-8-19-12-15(23)21-18(22-16(12)28)20-11(25)6-9-4-2-1-3-5-9/h1-5,8,10,13-14,17,24,26-27H,6-7H2,(H2,20,21,22,25,28)/t10-,13-,14-,17-/m1/s1

Upstream product

• 103-80-0 phenylacetyl chloride 
• 118-00-3 G 
• 263009-03-6 2'-O-[1-(4-Chlorophenyl)-4-ethoxypiperidin-4-yl]-2-N-(phenylacetyl)guanosine 
• 147490-73-1 2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-2-N-(phenylacetyl)guanosine 
• 64656-29-7 1-phenylacetoxy-1H-benzotriazole 

Downstream Products

• 163889-35-8 N-[9-((4aR,6R,7R,7aS)-2,2-Di-tert-butyl-7-hydroxy-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenyl-acetamide 
• 1013631-14-5 9-(2',3'-O-benzylidene-β-D-ribofuranosyl)-2-N-(phenylacetyl)-guanine 
• 132628-24-1 N-(9-{(2R,3R,4S,5S)-3,4-Dihydroxy-5-[9-(4-methoxy-phenyl)-9H-xanthen-9-ylsulfanylmethyl]-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenyl-acetamide 
• 147490-80-0 2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-2-N-(phenylacetyl)-5'-O-(9-phenylxanthen-9-yl)guanosine 3'-<(2-cyanoethyl)-N,N-diisopropylphosphoroamidite> 
• 147490-76-4 2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-2-N-(phenylacetyl)-5'-O-(9-phenylxanthen-9-yl)guanosine 
• 1053615-24-9 N-(9-{(2R,3R,3aR,9aR)-3-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-2-phenyl-acetamide 
• 147490-73-1 2'-O-<1-(2-fluorophenyl)-4-methoxypiperidin-4-yl>-2-N-(phenylacetyl)guanosine 
• 163889-47-2 N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-2-phenyl-acetamide 
• 163889-39-2 N-{9-[(4aR,6R,7R,7aR)-2,2-Di-tert-butyl-7-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-2-phenyl-acetamide 
• 163889-43-8 N-{9-[(2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-2-phenyl-acetamide 
• 309967-59-7 2'-O-[bis(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-5'-O-(4,4'-dimethoxytrityl)-2-N-phenylacetyl-6-O-(2-cyanoethyl)guanosine 
• 1053249-50-5 6-S-(2-cyanoethyl)-2'-O-(tert-butyldimethylsilyl)-2-N-phenylacetyl-6-thioguanosine 3',5'-bisphosphate tetrakis(2-cyanoethyl) ester 
• 309967-55-3 2'-O-[bis(2-cyano-1,1-dimethylethoxy)thiophosphoryl]-2-N-phenylacetyl-6-O-(2-cyanoethyl)guanosine 

Relevant articles and documents

Preparation N 2-phenylacetyl-D-guanylin improved method (by machine translation)

The invention relates to a preparation N 2-phenylacetyl-D-guanylin improved method, to the three a-based silicon-based protection in-quanosine D, adding phenyllacetyl chloride, 1-hydroxy benzotriazole, acetonitrile and reaction solution of pyri

Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

The comparative rates of acid-catalysed removal often 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined. The Royal Society of Chemistry 2000.

Base-modified enzymatic nucleic acid

An enzymatic nucleic acid having a modification selected from pyridin-4-one, pyridin-2-one, phenyl, pseudouracil, 2, 4, 6-trimethoxy benzene, 3-methyluracil, dihydrouracil, naphthyl, 6-methyl-uracil and aminophenyl.