title: Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin.
abstract: A novel oxalic amide-linked bisporphyrinate 1has been designed and synthesized, which shows chiral recognition ability for amino acid ethyl esters. The structure of complex 1·(D-Phe-OEt)(L-Phe-OEt) has been solved by X-ray crystallography. It reveals the following information: bisporphyrin unit adopts anti-configuration; compound 1forms 1: 2 complex with amino acid ethyl esters; one important hydrogen bond is formed between the coordinated nitrogen of amino acid ester and carbonyl oxygen in the amide group. The chiral recognition mechanism has been further investigated by UV-Vis spectra, (1)H NMR and DFT/TDDFT calculations.
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, PR China.
authors.forename: Jiaxun
authors.initials: J
authors.lastname: Jiang
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Feng
authors.forename: Baozhen
authors.initials: B
authors.lastname: Liu
authors.forename: Chuanjiang
authors.initials: C
authors.lastname: Hu
authors.forename: Yong
authors.initials: Y
authors.lastname: Wang
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D001665:Binding Sites; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D004952:Esters; D011166:Porphyrins