Convergent functional groups. 13. High-affinity complexation of adenosine derivatives within induced binding pockets

Autor:	M. Morgan Conn, Javier de Mendoza, Julius Rebek, Ghislain Deslongchamps
Rok vydání:	1993
Předmět:	Molecular model Chemistry medicine.drug_class Hydrogen bond Stacking Carboxamide General Chemistry Interaction energy Nuclear magnetic resonance spectroscopy Biochemistry Catalysis Inclusion compound Crystallography chemistry.chemical_compound Colloid and Surface Chemistry medicine Molecule
Zdroj:	Journal of the American Chemical Society. 115:3548-3557
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00062a020
Popis:	Receptors based upon 3,6-diaminocarbazole have been synthesized that bind to adenosine derivatives with an interaction energy of approximately 8 kcal/mol in CDCl 3 and over 3 kcal/mol in CD 3 OD. The purine nucleus is bound within a cavity by simultaneous Watson-Crick and Hoogsteen base-pairing, hydrogen bonding to N 3 , 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
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0535dfb1f305dc6ae31b7047bc30dcc0 https://doi.org/10.1021/ja00062a020 Zobrazit plný text záznamu