90358-07-9Relevant academic research and scientific papers
(2'--> 5')- and (3'--> 5')-Tubercidylyl-tubercidins - Synthesis via Phosphit Triester and Investigation of Secondary Structure
Seela, Frank,Ott, Johann,Hissmann, Edith
, p. 692 - 707 (2007/10/02)
The (2'--> 5')- and (3'--> 5')-linked dinucleoside monophosphates 3e and 2e of tubercidin were synthesized by condensation of the monomers 1c or 1b and 1a with dichloromethoxyphosphane.By 1H NMR studies it could be demonstrated that the conformation of these nucleobases is different from that in (3'--> 5')ApA and (2'--> 5')ApA.From thermodynamic parameters, as well as from hypochromicity, a stronger base-base interaction in 3e than in 2e was deduced.Single-strand specific nuclease S1 hydrolyses 2e at a much higher rate than (3'--> 5')ApA demonstrating that the enzyme is sensitive towards modification of the aglycone.Condensation of the 5'-deprotected dimer 3b with the monomer 1c followed by complete deprotection yields (2'--> 5')TupTupTu (4e), which is an analogue of (2'--> 5')ApApA, the triphosphate of which is antivirally active.
