Biomaterial Database

Selective recognition of sulfate ions by tripodal cyclic peptides functionalised with (thio)urea binding sites. 2012

Philip G Young, and Katrina A Jolliffe

School of Chemistry (F11), The University of Sydney, 2006 NSW, Australia.

A tripodal urea and tripodal thiourea with the same cyclic peptide core have been synthesised and their anion binding ability investigated. In CDCl(3), the tripodal urea self-associates whereas the thiourea does not. Neither compound shows self-association in the more polar 10% v/v DMSO-d(6)/CDCl(3). Both compounds bind strongly and selectively to sulfate ions in CDCl(3) and 10% v/v DMSO-d(6)/CDCl(3). This selectivity is attributed to a unique binding mode for sulfate, in which this tetrahedral anion forms nine hydrogen bonds to the receptors, with three of these coming from the amide protons of the cyclic peptide.

UI	MeSH Term	Description	Entries
D010456	Peptides, Cyclic	Peptides whose amino acid residues are linked together forming a circular chain. Some of them are ANTI-INFECTIVE AGENTS; some are biosynthesized non-ribosomally (PEPTIDE BIOSYNTHESIS, NON-RIBOSOMAL).	Circular Peptide,Cyclic Peptide,Cyclic Peptides,Cyclopeptide,Orbitide,Circular Peptides,Cyclopeptides,Orbitides,Peptide, Circular,Peptide, Cyclic,Peptides, Circular
D006860	Hydrogen Bonding	A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds.	Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D000838	Anions	Negatively charged atoms, radicals or groups of atoms which travel to the anode or positive pole during electrolysis.	Anion
D001665	Binding Sites	The parts of a macromolecule that directly participate in its specific combination with another molecule.	Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D013431	Sulfates	Inorganic salts of sulfuric acid.	Sulfate,Sulfates, Inorganic,Inorganic Sulfates
D013890	Thiourea	A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D019281	Dimerization	The process by which two molecules of the same chemical composition form a condensation product or polymer.	Dimerizations