Synthesis of new C 6 substituted peptidyl nucleosides. A mechanistic study
Mohamed M. Changalov and Dimiter D. Petkov,
Org. Commun. (2008), 1:2; 17-23
Laboratory of BioCatalysis, Institute of Organic Chemistry with Centre of Phytochemistry Bulgarian Academy of Sciences 1113 Sofia , Bulgaria
Abstract: The synthesis of four new peptidyl nucleosides is reported. The kinetic data obtained for the transesterification of 2'/3'-O-benzyloxycarbonyl-L-p-nitrophenylalanyl 5'-O-trityl ribonucleosides which contain different substituents at C 6 position of the purine residue indicates for different mechanisms of the transesterification reaction. The peptidyl nucleosides with an amino group at C 6 position and those lacking such group at that position have two distinctive mechanisms of transesterification .
Key words: Nucleosides; transesterification; tautomerization. |