Conjugate of palladium(II) complex and beta-cyclodextrin acts as a biomimetic peptidase

Nebojsa M Milović; Jovica D Badjić; Nenad M Kostić

doi:10.1021/ja038404p

Conjugate of palladium(II) complex and beta-cyclodextrin acts as a biomimetic peptidase

J Am Chem Soc. 2004 Jan 28;126(3):696-7. doi: 10.1021/ja038404p.

Authors

Nebojsa M Milović¹, Jovica D Badjić, Nenad M Kostić

Affiliation

¹ Department of Chemistry, Gilman Hall, Iowa State University, Ames, Iowa 50011-3111, USA.

PMID: 14733526
DOI: 10.1021/ja038404p

Abstract

We combined the newly discovered ability of [Pd(H2O)4]2+ to residue-selectively hydrolyze X-Pro bonds in peptides at 6 </= pH </= 9 with the known ability of beta-cyclodextrin to recognize aromatic side chains and synthesized a conjugate reagent that acts as a sequence-specific peptidase. This new reagent cleaved the Ser6-Pro7 amide bond in bradykinin at pH 7. ROESY 1H NMR spectra gave evidence for inclusion of the side chain of Phe8 in the beta-cyclodextrin cavity, the interaction that makes the cleavage sequence specific.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Biomimetic Materials / chemistry*
Biomimetic Materials / metabolism
Cyclodextrins / chemistry*
Cyclodextrins / metabolism
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides / chemistry
Oligopeptides / metabolism
Organometallic Compounds / chemistry
Organometallic Compounds / metabolism
Palladium / chemistry*
Peptide Hydrolases / chemistry*
Peptide Hydrolases / metabolism
beta-Cyclodextrins*

Substances

Cyclodextrins
Oligopeptides
Organometallic Compounds
beta-Cyclodextrins
Palladium
Peptide Hydrolases
betadex