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Tuning Zr(IV)-assisted peptide hydrolysis at near-neutral pH

Authors
Journal
Inorganic Chemistry Communications
1387-7003
Publisher
Elsevier
Publication Date
Volume
11
Issue
5
Identifiers
DOI: 10.1016/j.inoche.2008.01.026
Keywords
  • Amide Bond
  • Cleavage
  • 4
  • 13-Diaza-18-Crown-6
  • Ligand
  • Metal

Abstract

Abstract The present study has compared the effects of a total of 17 ligands on Zr(IV)-assisted hydrolysis of the dipeptide Gly–Gly (60 °C, pH 6.8–7.4, t = 4 h and t = 10 h). The macrocyclic azacrown ether ligands 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane and 1,4,10-trioxa-7,13-diazacyclopentadecane produced the overall highest amounts of hydrolysis, followed by the open-chain ligand 2-(2-aminoethoxy)-ethanol. While it was not necessary to have a ring structure to enhance Zr(IV) reactivity, the structural feature “ROCH 2CH 2OCH 2CH 2NR” appeared to contribute to increased levels of peptide cleavage.

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