84416-85-3

Basic information

• Product Name: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYTHYMIDINE-3'-(METHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE
• Synonyms: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYTHYMIDINE-3'-(METHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE;DMT-THYMIDINE O-METHYL PHOSPHORAMIDITE);dimethoxytrityl-thymidine phosphoramidite
• CAS NO: 84416-85-3
• Molecular Formula: C₃₈H₄₈N₃O₈P
• Molecular Weight: 721.78
• Mol File: 84416-85-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: Store at -20°C
• CAS DataBase Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYTHYMIDINE-3'-(METHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYTHYMIDINE-3'-(METHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE(84416-85-3)
• EPA Substance Registry System: 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYTHYMIDINE-3'-(METHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE(84416-85-3)

Safety Data

• Hazardous Substances Data: 84416-85-3(Hazardous Substances Data)

Upstream product

• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 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 
• 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

• 130856-82-5 3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-dithymidylyl-3',5'-O-methylphosphate 
• 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 articles and documents

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.

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.