328238-59-1

Basic information

• Product Name: 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate
• Synonyms: 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate
• CAS NO: 328238-59-1
• Molecular Weight: 762.174
• Mol File: 328238-59-1.mol

Chemical Properties

• CAS DataBase Reference: 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate(328238-59-1)
• EPA Substance Registry System: 2-amino-9-{(2R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]tetrahydrofuran-2-yl}-9H-purine-6-yl 2,4,6-triisopropylbenzenesulfonate(328238-59-1)

Safety Data

• Hazardous Substances Data: 328238-59-1(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 961-07-9 2'-Deoxyguanosine 
• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 51549-35-0 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 

Downstream Products

• 1572289-18-9 2'-deoxy-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosine 
• 1572289-19-0 2′-deoxy-5’-O-(4,4'-dimethoxytrityl)-6-N-{2-[(1,3-diaza-3-methyl-2-oxophenoxazin-9-yl)oxy]ethyl}-2-(phenoxyacetylamino)adenosin-3′-yl 2-cyanoethyl N,N-diisopropylphosphoramidite 
• 1609928-35-9 C₄₃H₅₉N₉O₈Si₂ 
• 1609928-34-8 C₅₂H₄₉N₉O₁₀ 

Relevant articles and documents

Mild and room temperature C-C bond forming reactions of nucleoside C-6 arylsulfonates

Palladium catalyzed cross coupling of nucleoside arylsulfonates and arylboronic acids has been accomplished under mild conditions and at room temperature. Among three structurally similar ligands that differ in their steric and electronic properties, one

LABELING METHOD FOR NUCLEIC ACID

Provided is a labeling method for nucleic acid including a reaction step for hybridizing a nucleic acid probe that has a nucleotide sequence complementary to that of a nucleic acid to be labeled and contains a reactive nucleobase derivative incorporated at a position complementary to that of a target nucleobase as a target of labeling in the nucleic acid to be labeled, to the nucleic acid to be labeled; a transferring step for transferring a transfer group contained in the reactive nucleobase derivative to the nucleotide residue containing the target nucleobase in the nucleic acid to be labeled; and a labeling step for labeling the transfer group transferred to the nucleotide residue with a radioactive material.

2,6-Diaminopurine nucleoside derivative of 9-ethyloxy-2-oxo-1,3- diazaphenoxazine (2-amino-Adap) for recognition of 8-oxo-dG in DNA

8-Oxo-2′-deoxyguanosine (8-oxo-dG) is a nucleoside resulting from oxidative damage and is known to be mutagenic. 8-Oxo-dG has been related to aging and diseases, including neurological disorders and cancer. Recently, we reported that a fluorescent nucleoside derivative, adenosine-1,3- diazaphenoxazine (Adap), forms a stable base pair with 8-oxo-dG in DNA with accompanying efficient quenching. In this study, a new Adap derivative having an additional 2-amino group on the adenosine moiety (2-amino-Adap) was designed with the anticipation of additional hydrogen bonding with the 8-oxo group of 8-oxo-dG. The properties of the ODN containing 2-amino-Adap were evaluated by measuring thermal stability and fluorescence quenching. In contrast to the previously designed Adap, the base-pairing and fluorescence quenching properties of 2-amino-Adap varied depending on the ODN sequence, and there was no clear indication of an additional hydrogen bond with 8-oxo-dG. Instead, the base pairing of 2-amino-Adap with dG was significantly destabilized compared with that of Adap with dG, resulting in improved selectivity for 8-oxo-dG in the human telomere DNA sequence. Thus, the telomere-targeting ODN probe containing 2-amino-Adap displayed selective, sensitive and quantitative detection of 8-oxo-dG in the human telomere DNA sequence in a light-up detection system using SYBR Green.

Nucleotides. Part LXVII. The 2-cyanoethyl and (2-cyanoethoxy)carbonyl group for base protection in nucleoside and nucleotide chemistry

The amino functions of the common 2′-deoxyribo- and ribonucleosides were blocked by the (2-cyanoethoxy) carbonyl group on treatment with 2-cyanoethyl carbonochloridate (5) or 1-[(2-cyanoethoxy)carbonyl] -3-methyl-1H-imidazolium chloride (6) leading to 7, 18.8, 19.9, and 20. In 2′-deoxyguanosine, the amide group was additionally blocked at the O° position by the 2-cyanoethyl (→ 27) and 2-(4-nitrophenyl)ethyl group (→ 31, 32). Comparative kinetic studies regarding the cleavage of the ce/ceoc and npe/npeoc group by β-elimination revealed valuable information about the case and sequential deprotection of the various blocking groups at different sites of the nucleobases. Besides the 5′-O-(dimethoxytrityl)-protected 3′-(2-cyanoethyl diisopropylphosphoramidites) 38 and 39 of N4-[(2-cyanoethoxy)carbonyl]-2′-deoxycytidine and N6-[(2-cyanoethoxy) carbonyl]-2′-deoxyadenosine, respectively, the N2-[(2-cyanoethoxy)carbonyl]-2′-deoxy-O°- [2-(4-nitrophenyl) ethyl]guanosine analog 40 is recommended as building block for oligo-2′-deoxyribonucleotide synthesis.