23583-44-0

Basic information

• Product Name: Thymidine, 5'-(hydrogen 4-morpholinylphosphonate)
• CAS NO: 23583-44-0
• Molecular Formula: C14H22N3O8P
• Molecular Weight: 391.318
• Mol File: 23583-44-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Thymidine, 5'-(hydrogen 4-morpholinylphosphonate)(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 5'-(hydrogen 4-morpholinylphosphonate)(23583-44-0)
• EPA Substance Registry System: Thymidine, 5'-(hydrogen 4-morpholinylphosphonate)(23583-44-0)

Safety Data

• Hazardous Substances Data: 23583-44-0(Hazardous Substances Data)

Upstream product

• 110-91-8 morpholine 
• 365-07-1 thymidine 5'-phosphate 
• 10588-31-5 tribromoacetyl bromide 
• 4124-31-6 trichloroacetic acid anhydride 
• 365-07-1 [5']thymidylic acid 

Downstream Products

• 1339937-99-3 C₁₇H₂₈N₂O₁₃P₂ 

Relevant articles and documents

Transition state in DNA polymerase β Catalysis: Rate-Limiting chemistry altered by base-pair configuration

Kinetics studies of dNTP analogues having pyrophosphate-mimicking β,β-pCXYp leaving groups with variable X and Y substitution reveal striking differences in the chemical transition-state energy for DNA polymerase β that depend on all aspects of base-pairing configurations, including whether the incoming dNTP is a purine or pyrimidine and if base-pairings are right (T*A and G*C) or wrong (T*G and G*T). Br?nsted plots of the catalytic rate constant (log(kpol)) versus pKa4 for the leaving group exhibit linear free energy relationships (LFERs) with negative slopes ranging from -0.6 to -2.0, consistent with chemical rate-determining transition-states in which the active-site adjusts to charge-stabilization demand during chemistry depending on base-pair configuration. The Br?nsted slopes as well as the intercepts differ dramatically and provide the first direct evidence that dNTP base recognition by the enzyme-primer-template complex triggers a conformational change in the catalytic region of the active-site that significantly modifies the rate-determining chemical step.

Reaction of Trifluoroacetic Anhydride with Thymidine 5'-Phosphate

The interaction of thymidine 5'-phosphate with trifluoroacetic anhydride in an aprotic solvent in the presence of a base is shown to give a mixed anhydride of thymidine 5'-phosphoric and trifluoroacetic acids.The anhydride reacts readily with high yield with various nucleophilic agents (morpholine, p-chlorophenol, pyrophosphate) to form nucleotide derivatives after pretreatment with nucleophilic catalysts (N-methylimidazole, 4-dimethylaminopyridine).Without these catalysts, nucleotide derivatives are not synthesized.A scheme of the reactions is proposed.Key words: trifluoroacetic anhydride, thymidine 5'-phosphate.