title: Chiral melamine derivatives: design, synthesis, and application to mass spectrometry-based chiral analysis.
abstract: A novel class of chiral melamine derivatives has been designed and synthesized. The ability of these compounds to perform chiral recognition toward 19 natural chiral alpha-amino acids has been investigated by electrospray ionization tandem mass spectrometry for the first time. The enantioselectivities of these new chiral selectors are encouraging. To elucidate some mechanism and regularity in the chiral recognition process using chiral melamine derivatives as chiral selectors, the effect of different noncovalent interactions caused by various chiral or achiral moieties in melamine derivatives on the chiral recognition in the gas phase has been studied at the same time. The result shows that electrostatic, hydrogen bond, pi-pi stacking, and steric interaction between selector and analyte play important roles in the association and enantioselective recognition of amino acids with the chiral melamine derivatives as chiral selectors. Enantiodiscrimination for analytes with different structures and properties could be improved by modifying substituents in melamine derivatives on purpose.
authors.affiliation: Beijing Institute of Pharmacology and Toxicology, 27 Taiping Road, Beijing 100850, P. R. China.
authors.forename: Qin
authors.initials: Q
authors.lastname: Liu
authors.forename: Shuzhen
authors.initials: S
authors.lastname: Zhang
authors.forename: Bidong
authors.initials: B
authors.lastname: Wu
authors.forename: Jifen
authors.initials: J
authors.lastname: Guo
authors.forename: Jianwei
authors.initials: J
authors.lastname: Xie
authors.forename: Mingsong
authors.initials: M
authors.lastname: Gu
authors.forename: Yimin
authors.initials: Y
authors.lastname: Zhao
authors.forename: Liuhong
authors.initials: L
authors.lastname: Yun
authors.forename: Keliang
authors.initials: K
authors.lastname: Liu
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D015195:Drug Design; D013058:Mass Spectrometry / Q000379:methods*; D015394:Molecular Structure; D013237:Stereoisomerism; D014227:Triazines / Q000032:analysis* / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D014227:Triazines; C011907:melamine