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‘Induced‐fit’ binding of an aryl phosphate by a macrobicyclic dicationic cyclodextrin derivative
Author(s) -
Hauser Steven L.,
Smith Paul J.
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.884
Subject(s) - chemistry , cyclodextrin , derivative (finance) , aryl , enthalpy , phosphate , binding energy , stereochemistry , computational chemistry , organic chemistry , thermodynamics , alkyl , physics , nuclear physics , financial economics , economics
Binding of an aryl phosphate ester with a dicationic cyclodextrin derivative was compared to that with an analogous, more conformationally restricted cyclodextrin. Binding of the latter host occurs with an unexpected increase in binding free energy, resulting from an increase in binding enthalpy. A structural basis for this difference involving ‘induced‐fit’ binding is proposed based on NMR experiments with the free host and the complex. Copyright © 2004 John Wiley & Sons, Ltd.