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The structures of complexes between amides and metal ions were examined by FAB mass spectrometry and collision-induced dissociation (CID). Zn2+ was coordinated by the amide carbonyl oxygen atom of N-tetradecylacetamide (1). In contrast, Ca2+ and Mg2+ were coordinated by the amide group of 1 in both the keto and enol forms. The catalytic role of Zn2+ at the active site of the hydrolases might partly be explained by the effective attack of Zn2+ on carbonyl oxygen atom of the scissile amide group.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Coordination of Divalent Metal Cation to Amide Group to Form Adduct Ion in FAB Mass Spectrometry: Implication of Zn2+ in Enzymatic Hydrolysis of Amide Bond