Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding.
[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.
Chin
Jik
J
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada. jchin@chem.utoronto.ca
Kim
Dong Chan
DC
Kim
Hae-Jo
HJ
Panosyan
Francis B
FB
Kim
Kwan Mook
KM
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
D000447:Aldehydes; D000596:Amino Acids; D007097:Imines; D007202:Indicators and Reagents