CONVERGENT FUNCTIONAL-GROUPS .13. HIGH-AFFINITY COMPLEXATION OF ADENOSINE DERIVATIVES WITHIN INDUCED BINDING POCKETS

Citation
Mm. Conn et al., CONVERGENT FUNCTIONAL-GROUPS .13. HIGH-AFFINITY COMPLEXATION OF ADENOSINE DERIVATIVES WITHIN INDUCED BINDING POCKETS, Journal of the American Chemical Society, 115(9), 1993, pp. 3548-3557
Citations number
51
Categorie Soggetti
Chemistry
ISSN journal
00027863
Volume
115
Issue
9
Year of publication
1993
Pages
3548 - 3557
Database
ISI
SICI code
0002-7863(1993)115:9<3548:CF.HCO>2.0.ZU;2-L
Abstract
Receptors based upon 3,6-diaminocarbazole have been synthesized that b ind to adenosine derivatives with an interaction energy of approximate ly 8 kcal/mol in CDCl3 and over 3 kcal/mol in CD3OD. The purine nucleu s is bound within a cavity by simultaneous Watson-Crick and Hoogsteen base-pairing, hydrogen bonding to N3, and stacking on both of its arom atic faces. Hydrogen bond interactions can be estimated at approximate ly 0.5-0.75 kcal/mol in methanol. The structure of the complex in solu tion has been deduced through binding assays of incremental derivative s, one- and two-dimensional NMR studies, and molecular modeling.