Recognition and sequestration of ω-fatty acids by a cavitand receptor.
Proc Natl Acad Sci U S A
; 112(36): 11181-6, 2015 Sep 08.
Article
in En
| MEDLINE
| ID: mdl-26305974
ABSTRACT
One of the largest driving forces for molecular association in aqueous solution is the hydrophobic effect, and many synthetic receptors with hydrophobic interiors have been devised for molecular recognition studies in water. Attempts to create the longer, narrower cavities appropriate for long-chain fatty acids have been thwarted by solvophobic collapse of the synthetic receptors, giving structures that have no internal spaces. The collapse generally involves the stacking of aromatic panels onto themselves. We describe here the synthesis and application of a deep cavitand receptor featuring "prestacked" aromatic panels at the upper rim of the binding pocket. The cavitand remains open and readily sequesters biologically relevant long-chain molecules-unsaturated ω-3, -6, and -9 fatty acids and derivatives such as anandamide-from aqueous media. The cavitand exists in isomeric forms with different stacking geometries and n-alkanes were used to characterize the binding modes and conformational properties. Long alkyl chains are accommodated in inverted J-shaped conformations. An analogous cavitand with electron-rich aromatic walls was prepared and comparative binding experiments indicated the role of intramolecular stacking in the binding properties of these deep container molecules.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Resorcinols
/
Ethers, Cyclic
/
Fatty Acid-Binding Proteins
/
Fatty Acids, Unsaturated
Language:
En
Journal:
Proc Natl Acad Sci U S A
Year:
2015
Document type:
Article
Affiliation country:
Italia