title: Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding.
abstract: [structure: see text] A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada. jchin@chem.utoronto.ca
authors.forename: Jik
authors.initials: J
authors.lastname: Chin
authors.forename: Dong Chan
authors.initials: DC
authors.lastname: Kim
authors.forename: Hae-Jo
authors.initials: HJ
authors.lastname: Kim
authors.forename: Francis B
authors.initials: FB
authors.lastname: Panosyan
authors.forename: Kwan Mook
authors.initials: KM
authors.lastname: Kim
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D007097:Imines / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D007097:Imines; D007202:Indicators and Reagents