ABSTRACT
A receptor for carboxylic acids which combines an oxyanion-hole structure with electrostatic forces has been prepared. X-ray diffraction studies have been carried out to evaluate the geometry of both the free receptor and its associated species with several carboxylic acids and many different arrangements have been discovered for the H-bond pattern in the associated species.
ABSTRACT
A molecular receptor has been synthesized joining an aza-crown ether with a chiral chromane which mimics the oxyanion hole of the enzymes. With this receptor an apolar host-guest complex with zwitterionic alanine has been achieved through the formation of up to seven H-bonds. This complex allows the extraction of aqueous alanine to a chloroform phase, while other natural amino acids are poorly extracted or are not extracted at all. Due to the chiral nature of the receptor, enantioselective extraction from the aqueous alanine solution to a chloroform phase takes place. X-Ray analysis combined with anisotropic effects, NOE and CD studies revealed the absolute configuration of both strong and weak complexes. Modelling studies also support the proposed structures. The presence of an oxyanion-hole motif in this structure was corroborated by X-ray diffraction studies.
Subject(s)
Alanine/isolation & purification , Aza Compounds/chemistry , Chromans/chemistry , Crown Ethers/chemistry , Alanine/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Models, Molecular , Molecular Conformation , StereoisomerismABSTRACT
Administration of enantiomerically pure ß-adrenergic agonists and antagonists increases their activity and reduces side effects. We report here a small-molecule artificial receptor (SMAR) that, by mimicking the ß-adrenergic receptor, is able to enantioselectively extract commercial ß-adrenergic interacting drugs. The selectivity is justified according to DFT calculations and X-ray diffraction experiments.
Subject(s)
Adrenergic beta-Agonists/pharmacology , Adrenergic beta-Antagonists/pharmacology , Receptors, Adrenergic, beta/chemistry , Receptors, Artificial/metabolism , Humans , Quantum Theory , StereoisomerismABSTRACT
The combination of a 1,3-ketoenol system and two pyridine molecules attached as sulfonamide and carboxamide to a benzofuran skeleton allows the preparation of a novel chiral receptor for zwitterionic phenylalanine association. Interestingly, no crown-ether, urea or guanidinium are necessary to carry out the extraction of amino acids from the aqueous solution, which constitutes a breakthrough in comparison with other receptors for zwitterionic amino acid extraction.
Subject(s)
Phenylalanine/chemistry , Magnetic Resonance Spectroscopy , Models, MolecularABSTRACT
A chiral chromane receptor has been synthesized which mimics the oxyanion hole of the enzymes. In this receptor H-bonds and cation-π interactions team up to generate an apolar host-guest complex with zwitterionic proline. This complex allows the extraction of only proline to a chloroform phase, while no other natural amino acids are extracted. Due to the chiral nature of the receptor, enantioselective extraction from the aqueous proline solution to a chloroform phase takes place. L-Proline provided an easy method to resolve the receptor racemic mixture, while anisotropic effects, NOE and CD studies revealed the absolute configuration of the receptor. Modelling studies also support the proposed structures. The presence of an oxyanion-hole motif in this structure was corroborated by X-ray diffraction studies.
Subject(s)
Benzopyrans/chemistry , Phenylurea Compounds/chemistry , Proline/chemistry , Chloroform/chemistry , Crystallography, X-Ray , Models, Molecular , Molecular Structure , Proline/isolation & purificationABSTRACT
A new chiral benzofuran receptor has been synthesized and its properties in the association of amino acid derivatives have been studied. X-ray structures were obtained and these corroborate the presence of an oxyanion-hole motif in these structures.
Subject(s)
Anions/chemistry , Benzofurans/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Models, Molecular , StereoisomerismABSTRACT
A series of bi- and tricyclic ß-lactam compounds was synthesized and evaluated as inhibitors of cleavage of synthetic substrates in vitro by the serine proteases Human Leukocyte Elastase (HLE), Human Leukocyte Proteinase 3 (HLPR3) and Porcine Pancreatic Elastase (PPE). The obtained results have permitted us to describe a homobenzocarbacephem compound as HLE and HLPR3 inhibitor, to observe the positive effect that the styryl group exerts on the HLE inhibitory activity in polycyclic ß-lactam compounds and to conclude that the hydroxyl function decreases the HLE inhibitory activity or rules it out completely.
