Chiral Recognition of Amino Acids and Dipeptides by a Water-Soluble Zinc Porphyrin
- 1 February 2004
- journal article
- Published by American Chemical Society (ACS) in Inorganic Chemistry
- Vol. 43 (4), 1211-1213
- https://doi.org/10.1021/ic0302837
Abstract
A chiral water-soluble zinc porphyrin was optically resolved on a chiral HPLC column, and the binding of chiral amino acids and peptides to each of the enantiomers was examined spectrophotometrically in basic aqueous solution. The binding data apparently indicated that the zinc porphyrin has chiral selectivity for amino acids and dipeptides. This was reasonably explained in terms of the triple cooperation of coordination, Coulomb, and steric interactions of the chiral amino carboxylates with the porphyrin. A compensatory relationship among the thermodynamic parameters for chiral recognition was also shown.Keywords
This publication has 14 references indexed in Scilit:
- Hydrophobic environment of gable-type bisporphyrin receptors in water promotes binding of amines and oligopeptidesChemical Communications, 2002
- Porphyrin-Based Peptide Receptors: Syntheses and NMR AnalysisChemistry – A European Journal, 2002
- Water-Soluble Zinc Porphyrins as Receptors for Amino CarboxylatesChemistry Letters, 2001
- Anion receptor chemistry: highlights from 1999Coordination Chemistry Reviews, 2001
- Hydrophobic Interactions in Metalloporphyrin−Peptide ComplexesInorganic Chemistry, 2000
- Chiral Recognition Thermodynamics of β-Cyclodextrin: The Thermodynamic Origin of Enantioselectivity and the Enthalpy−Entropy Compensation EffectJournal of the American Chemical Society, 2000
- Porphyrin Receptors for Amines, Amino Acids, and Oligopeptides in WaterJournal of the American Chemical Society, 1999
- Amine binding to water-soluble zinc porphyrins bearing a hydrophobic binding pocketJournal of the Chemical Society, Perkin Transactions 2, 1999
- Molecular recognition in chemistry and biology as viewed from enthalpy-entropy compensation effectPublished by Elsevier ,1997
- Structural studies of metalloporphyrins. Part XI: Complexes of water-soluble zinc(II) porphyrins with amino acids: Influence of ligand-ligand interactions on the stability of the complexesJournal of Inorganic Biochemistry, 1990