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.
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.
Kobayashi
Hisayoshi
H
Institute of Molecular & Cellular Biosciences, The University of Tokyo, Yayoi, Tokyo, Japan.
Morisaki
Naoko
N
Miyachi
Hiroyuki
H
Hashimoto
Yuichi
Y
D000577:Amides / Q000737:chemistry*; D002118:Calcium / Q000737:chemistry; D002413:Cations, Divalent / Q000737:chemistry*; D006867:Hydrolases / Q000737:chemistry; D006868:Hydrolysis; D007202:Indicators and Reagents; D008274:Magnesium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D015032:Zinc / Q000737:chemistry*
D000577:Amides; D002413:Cations, Divalent; D007202:Indicators and Reagents; D006867:Hydrolases; D008274:Magnesium; D015032:Zinc; D002118:Calcium