ISSN:
0947-6539
Keywords:
ab initio calculations
;
binding studies
;
crystal packing
;
drug design
;
hydrogen bonds
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In the design of novel protein ligands one of the major challenges is the replacement of functional groups to modify and improve the binding characteristics. Often nitrogen- and oxygen-containing groups are exchanged, or both atoms occur in a competitive situation. We have investigated the hydrogen-bonding abilities of oxygen atoms covalently bound to two non-hydrogen atoms of which at least one is formally assigned to an sp2-type hybridization. In particular, examples in which such oxygen atoms compete with nitrogen atoms in the same molecular segment have been studied. Based on interaction energies obtained from ab initio calculations for complexes of these molecules with water, the oxygen atoms can be classified as rather weak hydrogen-bond acceptors; nitrogen atoms present in the same fragment exhibit much stronger interaction energies. The ab initio results are confirmed by the relative frequencies with which oxygen and nitrogen atoms are found to be involved in hydrogen bonding in the crystal structures of organic molecules containing the fragments of interest.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19960021206
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