148582-32-5Relevant articles and documents
Convergent functional groups. 13. High-affinity complexation of adenosine derivatives within induced binding pockets
Conn, M. Morgan,Deslongchamps, Ghislain,De Mendoza, Javier,Rebek Jr., Julius
, p. 3548 - 3557 (2007/10/02)
Receptors based upon 3,6-diaminocarbazole have been synthesized that bind to adenosine derivatives with an interaction energy of approximately 8 kcal/mol in CDCl3 and over 3 kcal/mol in CD3OD. The purine nucleus is bound within a cavity by simultaneous Watson-Crick and Hoogsteen base-pairing, hydrogen bonding to N3, and stacking on both of its aromatic faces. Hydrogen bond interactions can be estimated at approximately 0.5-0.75 kcal/mol in methanol. The structure of the complex in solution has been deduced through binding assays of incremental derivatives, one- and two-dimensional NMR studies, and molecular modeling.