242475-43-0

Basic information

• Product Name: 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine
• Synonyms: 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine
• CAS NO: 242475-43-0
• Molecular Weight: 925.271
• Mol File: 242475-43-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine(242475-43-0)
• EPA Substance Registry System: 5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-4-O-triisopropylphenylsulfonyl thymidine(242475-43-0)

Safety Data

• Hazardous Substances Data: 242475-43-0(Hazardous Substances Data)

Upstream product

• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 80971-33-1 5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 50-89-5 thymidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 244307-10-6 N⁴-ureido-5'-O-4,4'-dimethoxytrityl-5-methyl-2'-deoxycytidine 
• 244307-08-2 N⁴-ureido-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine 
• 244307-09-3 N⁴-(N²-acetamidoureido)-5'-O-4,4'-dimethoxytrityl-3'-O-tertbutyldimethylsilyl-5-methyl-2'-deoxycytidine 

Relevant articles and documents

Intermolecular 'cross-torque': The N4-cytosine propargyl residue is rotated to the 'CH'-edge as a result of Watson-Crick interaction

Propargyl groups are attractive functional groups for labeling purposes, as they allow CuAAC-mediated bioconjugation. Their size minimally exceeds that of a methyl group, the latter being frequent in natural nucleotide modifications. To understand under which circumstances propargyl-containing oligodeoxynucleotides preserve base pairing, we focused on the exocyclic amine of cytidine. Residues attached to the exocyclic N4 may orient away from or toward the Watson-Crick face, ensuing dramatic alteration of base pairing properties. ROESY-NMR experiments suggest a uniform orientation toward the Watson-Crick face of N4-propargyl residues in derivatives of both deoxycytidine and 5-methyl-deoxycytidine. In oligodeoxynucleotides, however, UV-melting indicated that N4-propargyl-deoxycytidine undergoes standard base pairing. This implies a rotation of the propargyl moiety toward the 'CH'-edge as a result of base pairing on the Watson-Crick face. In oligonucleotides containing the corresponding 5-methyl-deoxycytidine derivative, dramatically reduced melting temperatures indicate impaired Watson-Crick base pairing. This was attributed to a steric clash of the propargyl moiety with the 5-methyl group, which prevents back rotation to the 'CH'-edge, consequently preventing Watson-Crick geometry. Our results emphasize the tendency of an opposing nucleic acid strand to mechanically rotate single N4-substituents to make way for Watson-Crick base pairing, providing no steric hindrance is present on the 'CH'-edge.