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The Interaction of Zinc(II) and Hydroxamic Acids and a Metal‐Triggered Lossen Rearrangement
Author(s) -
Ducháčková Lucie,
Roithová Jana
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901645
Subject(s) - acetohydroxamic acid , chemistry , deprotonation , hydroxamic acid , zinc , acetic acid , medicinal chemistry , stereochemistry , organic chemistry , enzyme , ion , urease
The structure and reactivity of a complex of zinc(II), water, acetic acid, and acetohydroxamic acid, in which one of the acids is deprotonated, is investigated by means of mass spectrometry, labeling studies, and density functional calculations to unravel the exceptional binding properties of hydroxamic acids towards zinc‐containing enzymes at the molecular level. It is shown that acetohydroxamic acid is deprotonated in the complex, whereas acetic acid is present in its neutral form. The binding energies of the ligands towards zinc increase in the following order: water