86137-72-6

Basic information

• Product Name: 2'-Deoxy-6-O-[2-(4-nitrophenyl)ethyl]guanosine
• Synonyms: 2'-Deoxy-6-O-[2-(4-nitrophenyl)ethyl]guanosine;2'-Deoxy-O6-[2-(4-nitrophenylethyl)]guanosine
• CAS NO: 86137-72-6
• Molecular Formula: C₁₈H₂₀N₆O₆
• Molecular Weight: 416.39
• Mol File: 86137-72-6.mol

Chemical Properties

• Appearance: /
• Density: 1.71
• CAS DataBase Reference: 2'-Deoxy-6-O-[2-(4-nitrophenyl)ethyl]guanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Deoxy-6-O-[2-(4-nitrophenyl)ethyl]guanosine(86137-72-6)
• EPA Substance Registry System: 2'-Deoxy-6-O-[2-(4-nitrophenyl)ethyl]guanosine(86137-72-6)

Safety Data

• Hazardous Substances Data: 86137-72-6(Hazardous Substances Data)

Upstream product

• 132183-38-1 2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²,3',5'-triacetylguanosine 
• 82921-55-9 N²,3',5'-triisobutyryl-O⁶-p-nitrophenylethyl-2'-deoxyguanosine 
• 108310-92-5 2-amino-6-(2-(p-nitrophenyl)ethyloxy)-9-[2'-deoxy-β-D-erythropentofuranosyl]purine diacetate 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 129184-64-1 3',5'-bis-O-trimethylsilyl-2'-deoxyguanosine 
• 961-07-9 2'-Deoxyguanosine 
• 69992-10-5 3',5'-di-O-acetyl-2'-deoxyguanosine 
• 4318-05-2 2-(acetylamino)-9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one 
• 961-07-9 2'-deoxyguanosine 
• 82921-42-4 2'-deoxy-N²-isobutyrylguanosine 3',5'-diisobutyrate 

Downstream Products

• 132183-39-2 2-fluoro-O⁶-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine 
• 195875-07-1 6-O-(4-nitrophenylethyl)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyguanosine 
• 153527-28-7 5'-O-(4,4'-Dimethoxytrityl)-6-O-[2-(4-nitrophenyl)ethyl]-2'-deoxy-2-fluoroinosine 
• 259141-09-8 5'-O-(4,4'-dimethoxytrityl)-6-O-(4-nitrophenylethyl)-2-N-(4,9,13-triazatridecane-1-yl)-2'-deoxyguanosine 
• 259141-10-1 5'-O-(4,4'-dimethoxytrityl)-6-O-(4-nitrophenylethyl)-2-N-[tris(N,N',N''-trifluoroacetyl)-4,9,13-triazatridecane-1-yl]-2'-deoxyguanosine 
• 81144-43-6 5'-O-(p,p'-dimethoxytrityl)-2'-deoxyguanosine 
• 199800-46-9 2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine 
• 199800-59-4 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine 
• 226894-56-0 (2R,3S,5R)-5-{2-Amino-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-ol 
• 132209-52-0 2'-Deoxy-O⁶-<(p-nitrophenyl)ethyl>-N²-(1-pyrenylmethyl)guanosine 
• 132209-53-1 2'-Deoxy-5'-(p-dimethoxytrityl)-N²-(1-pyrenylmethyl)guanosine 
• 132183-41-6 (+/-)-N²-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)guanosine phosphoramidite 
• 1080623-91-1 3'-O-acetyl-2'-deoxy-2-fluoro-O₆-[2-(4-nitrophenyl)ethyl]inosine 

Relevant articles and documents

Synthesis and evaluation of pyrrole polyamide-2′-deoxyguanosine 5′-phosphate hybrid

Pyrrole polyamide-2′-deoxyguanosine 5′-phosphate hybrid (Hybrid 4) was synthesized and evaluated in terms of the inhibition of mouse mammary carcinoma FM3A cell growth. Hybrid 4 was found to exhibit dose-dependent inhibition of cell growth.

Synthetic oligonucleotide combinatorial libraries. 3. Synthesis of polyaminonucleosides

Synthesis of polyamino-2'deoxynucleosides was studied. A synthesis of 2'-deoxyadenosine and 2'-deoxyguanosine derivatives carrying a protected spermine moiety at N-6 and N-2 positions respectively is described using unprotected polyamines as substrates. T

Nucleotides: Part LXI: Phthaloyl strategy: A new concept of oligonucleotide synthesis

A new alternative strategy of oligonucleotide synthesis was developed by use of the phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9-12). This approach combines the advantages of cheap and easily accessible monomeric building blocks (see 17- 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

N2- and C8-substituted oligodeoxynucleotides with enhanced thrombin inhibitory activity in vitro and in vivo.

2'-Deoxyguanosine (G) analogues carrying various hydrophobic substituents in the N2 and C8 positions were synthesized and introduced through solid-phase synthesis into 15-mer oligodeoxynucleotide, GGTTGGTGTGGTTGG, which forms a chairlike structure consist

Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons

An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry

Syntheses of polycyclic aromatic hydrocarbon-nucleoside and oligonucleotide adducts specifically alkylated on the amino functions of deoxyguanosine and deoxyadenosine

Efficient syntheses of 1-pyrenylmethyl-mononucleoside adducts with the hydrocarbon moiety atached to the exocyclic amino functions of deoxyguanosine and deoxyadenosine are described.

THE p-NITROPHENYLETHYL (NPE) GROUP. A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES

The syntheses of new monomeric building blocks for oligonucleotide synthesis via the phosphotriester approach containing the p-nitrophenylethyl group for phosphate and aglycone protection are described.Blocking of the amide function in guanosines at O6 can be achieved by the Mitsunobu reaction forming the corresponding O6-p-nitrophenylethyl derivatives (4,5,10).Sugar-protected thymidine (16) and uridine (17) have been alkylated at O4 in an SN1-type reaction by p-nitrophenylethyl iodide-silver carbonate in benzene to form the O4-p-nitrophenylethyl derivatives (18,19).Protection of the amino group in 2'-deoxycytidine (25) and cytidine (26) can be performed directly by 1-(p-nitrophenylethoxycarbonyl)-benzotriazole in DMF to obtain the corresponding carbamates (27,28) as a new type of N4-acylated cytidine derivative. p-Nitrophenylethoxycarbonylation of the amino group in 2'-deoxyadenosine (33) and adenosine (34) requires previous sugar protection by acyl or silyl groups and can then be achieved by p-nitrophenylethyl chloroformate or better by 1-methyl-3-p-nitrophenylethoxycarbonylimidazolium chloride to form N6-p-nitrophenylethoxycarbonyladenosines (38,39,40,42).The various p-nitrophenylethyl blocking groups are stable under mild hydrolytic conditions (e.g. ammonia and triethylamine) but can be cleaved selectively by DBU or DBN in aprotic solvents. 5'-O-Monomethoxytritylation (12,29,43) as well as phosphorylations at the 3'-OH group can be effected to give the corresponding 3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphotriesters (13,22,30,44) also in high yields.Oximate cleavage of the latter compounds to the phosphodiesters (14,24,32,46) and detritylation to the 5'-unblocked phosphotriesters (15,23,31,45) do not affect the aglycone protecting groups, thereby demonstrating their general versatility.The newly synthesized compounds have been characterized on the basis of their elementary analyses (C,N,H), and UV- and 1H-HMR-spectra.

SYNTHESIS OF O6-p-NITROPHENYLETHYL GUANOSINE AND 2'-DEOXYGUANOSINE DERIVATIVES

The p-nitrophenylethyl group is introduced into the O6-position of 2'-deoxyguanosine and guanosine via the Mitsunobu-reaction to yield valuable building blocks for oligonucleotide syntheses.