Influence of the amino acid side chain on peptide bond hydrolysis catalyzed by a dimeric Zr(IV)-substituted Keggin type polyoxometalate
作者： Hong Giang T. Ly , Gregory Absillis , Tatjana N. Parac-Vogt
DOI: 10.1039/C5NJ00561B
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摘要: Peptide bond hydrolysis of 18 different dipeptides, divided into four groups depending on the nature amino acid side chain, by dimeric Zr(IV)-substituted Keggin type polyoxometalate (POM) (Et2NH2)8[{α-PW11O39Zr-(μ-OH)(H2O)}2]·7H2O (1) was studied means kinetic experiments and 1H/13C NMR spectroscopy. The observed rate constants highly depend bulkiness chemical X chain. X-Ser X-Thr dipeptides showed increased reactivity due to intramolecular nucleophilic attack hydroxyl group in chain amide carbon, resulting a reactive ester intermediate. A similar effect which acted as an internal nucleophile for Gly-Asp. Interestingly, presence 1 deamidation Gly-Asn Gly-Gln Gly-Asp Gly-Glu observed. Dipeptides containing positively charged chains were hydrolyzed at higher rates electrostatic interactions between negatively POM surface positive chains.
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