152873-41-1Relevant articles and documents
Synthesis, Enzymatic Stability and Base-pairing Properties of Oligothymidylates Containing Thymidine Dimers with Different N-Substituted Guanidine Linkages
Vandendriessche, Frank,Aerschot, Arthur Van,Voortmans, Martine,Janssen, Gerard,Busson, Roger,et al.
, p. 1567 - 1576 (2007/10/02)
Reaction of 5'-amino-5'deoxythymidine 1 with different S,S-dimethyl-N-substituted dithiocarbonimidates 2a-j afforded the N-substituted isothioureas 3a-j which, on further reaction with 3'-amino-3'-deoxythymidine 4 in the presence of AgNO3, led to thymidine dimers 5a-j with different N-substituted guanidine linkages.The dimer with a thiourea linkage (compound 9) was also prepared.Dimers 5a-h were incorporated at different positions in oligothymidylates by using phosphoramidite chemistry.Attempts to incorporate compounds 5i,j and 9 led to complex mixtures. 3'-Protected oligonucleotides showed somewhat higher stability to snake venom phosphodiesterase.Melting experiments revealed that the N-methylsulfonyl-substituted guanidine linkage best mimics the natural phosphodiester bridge.The fluorescence properties of oligonucleotides with dimer 5f were studied in view of its potential use as a non-radioactive label for DNA.