84416-85-3

Upstream product

• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 67-56-1 methanol 
• 104655-84-7 5‘-O-dimethoxytrityl-2’-deoxyribothymidine 3‘-O-phosphorodiamidite 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 50-89-5 thymidine 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 108-18-9 diisopropylamine 
• 121667-95-6 monochloro-N,N-diisopropylaminothiomethoxyphosphine 
• 92611-10-4 bis(N,N-diisopropylamino)methoxyphosphine 
• 86030-43-5 N,N-diisopropylmethylphosphonamidic chloride 

Downstream Products

• 93134-61-3 C₄₈H₅₀N₅O₁₄P 
• 1360780-23-9 C₅₅H₆₆N₆O₁₅P₂ 
• 1360780-18-2 C₅₆H₅₆N₅O₁₆P 
• 2476-56-4 5'-d(TpTp)-3' 
• 141928-26-9 5'-O-(N⁶-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate 
• 141955-64-8 5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate 
• 130767-64-5 Thiophosphoric acid O-[(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester O'-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester 
• 160343-20-4 C₅₁H₅₇N₅O₁₉P₂ 
• 160343-28-2 C₃₀H₃₉N₅O₁₇P₂ 
• 87007-52-1 C₄₂H₄₇N₄O₁₄P 

Relevant academic research and scientific papers

Cytotoxic and mutagenic properties of alkyl phosphotriester lesions in Escherichia coli cells

Exposure to many endogenous and exogenous agents can give rise to DNA alkylation, which constitutes a major type of DNA damage. Among the DNA alkylation products, alkyl phosphotriesters have relatively high frequencies of occurrence and are resistant to repair in mammalian tissues. However, little is known about how these lesions affect the efficiency and fidelity of DNA replication in cells or how the replicative bypass of these lesions is modulated by translesion synthesis DNA polymerases. In this study, we synthesized oligodeoxyribonucleotides containing four pairs (Sp and Rp) of alkyl phosphotriester lesions at a defined site, and examined how these lesions are recognized by DNA replication machinery in Escherichia coli cells. We found that the Sp diastereomer of the alkyl phosphotriester lesions could be efficiently bypassed, whereas the Rp counterparts moderately blocked DNA replication. Moreover, the Sp-methyl phosphotriester induced TT→GT and TT→GC mutations at the flanking TT dinucleotide site, and the induction of these mutations required Ada protein, which is known to remove efficiently the methyl group from the Sp-methyl phosphotriester. Together, our study provided a comprehensive understanding about the recognition of alkyl phosphotriester lesions by DNA replication machinery in cells, and revealed for the first time the Ada-dependent induction of mutations at the Sp-methyl phosphotriester site.

Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability

A spermine-conjugated ethyl phosphotriester oligonucleotide was obtained by solid-phase synthesis based on phosphoramidite chemistry. The ethyl phosphotriester linkage was robust to exonuclease digestion and stable in fetal bovine serum. Cell membrane permeability of the spermine-conjugated ethyl phosphotriester oligonucleotide was studied by fluorescence experiments. The effective cell penetrating potency of the spermine-conjugated ethyl phosphotriester oligonucleotide was determined by confocal laser scanning microscopy and measurement of intracellular fluorescence intensity.

Rapid and efficient syntheses of phosphorylated dinucleotides

Nine or ten-step solution phase syntheses of the dimers dpApA, dApAp, dpTpT and dTpTp in 0.1-0.5 g amounts, in overall yields of 49%, 45%, 32%, and 20% respectively, are described. The synthetic intermediates were characterized by 1H and 3

NEW APPROACH TO THE SYNTHESIS OF DEOXYNUCLEOSIDE-PHOSPHORAMIDITE DERIVATIVES

A new method for the synthesis of deoxyribonucleoside-phosphoramidite via an intermediate, 5'-O-dimethoxytritylthymidine-3'-O-diisopropylamino-phosphorochloridite, is reported.By using this method, several deoxyribonucleoside phosphoramidite derivatives with different protecting groups at phosphorus including P-S and P-N bond besides P-O bond were synthesized.

New Approach to the Synthesis of Deoxyribonucleoside Phosphoramidite Derivatives

The deoxyribonucleoside phosphoramidites with various protecting groups at phosphorus have been prepared rapidly in good yields in one-pot reaction from bis(diisopropylamino)chlorophosphine as a new phosphitylating agent without isolation of bis(diisopropylamino)alkoxyphosphines.

Chiral Phosphate in d(CpA) and d(TpA): Synthesis via Phosphite Triesters and Assignment of Configuration

The dinucleoside monophosphates d(TpA) (11a) and d(CpA) (19a) - both chirally labeled with 18O at phosphorus and representing cleavage sites in a number of restriction endonuclease recognition sequences - have been synthesized via the fully protected phos

AN INVESTIGATION OF SEVERAL DEOXYNUCLEOSIDE PHOSPHORAMIDITES USEFUL FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES

Various deoxynucleoside N,N-dialkylaminomethoxyphosphines were examined for stability and reactivity in deoxyoligonucleotide synthesis.Of those examined, the N-morpholino and N,N-diisopropylamino derivatives most completely satisfied all criteria.