Preparation of single-enantiomer biofunctional molecules with (S)-2-methoxy-2-(1-naphthyl)propanoic acid.
(RS)-beta-Ionol and (RS)-2-methyl-4-octanol were resolved by using (S)-2-methoxy-2-(1-naphthyl)propanoic acid [(S)-MalphaNP acid]. The specific stereochemistry of each MalphaNP ester was elucidated by 2D NMR analyses, and shielding by the 1-naphthyl group was observed in both the 1H- and 13C-NMR spectra. Solvolysis of the individual (S)-MalphaNP esters gave four single-enantiomer alcohols. The normal-phase HPLC elution order of each MalphaNP ester is also discussed.
Ichikawa
Akio
A
Division of Insect Sciences, National Institute of Agrobiological Sciences, Ibaraki, Japan. ichikawa@affrc.go.jp
Ono
Hiroshi
H
D000438:Alcohols / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds
D000438:Alcohols; D004952:Esters; D009281:Naphthalenes; D011422:Propionates; D013438:Sulfhydryl Compounds; C499260:2-methoxy-2-(1-naphthyl)propionic acid; C029658:propionic acid