title: Highly efficient chiral resolution of DL-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions.
abstract: An excellent chiral symmetry-breaking spontaneous enantiomeric resolution phenomenon, denoted preferential enrichment, was observed on recrystallization of the 1:1 cocrystal of dl-arginine and fumaric acid, which is classified as a racemic compound crystal with a high eutectic ee value (>95 %), under non-equilibrium crystallization conditions. On the basis of temperature-controlled video microscopy and in situ time-resolved solid-state (13) C NMR spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed.
authors.affiliation: Graduate School of Human and Environmental Studies, Kyoto University, Yoshida Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-7915.
authors.forename: Sekai
authors.initials: S
authors.lastname: Iwama
authors.forename: Kazunori
authors.initials: K
authors.lastname: Kuyama
authors.forename: Yuko
authors.initials: Y
authors.lastname: Mori
authors.forename: Kochunnoonny
authors.initials: K
authors.lastname: Manoj
authors.forename: Rajesh G
authors.initials: RG
authors.lastname: Gonnade
authors.forename: Katsuaki
authors.initials: K
authors.lastname: Suzuki
authors.forename: Colan E
authors.initials: CE
authors.lastname: Hughes
authors.forename: P Andrew
authors.initials: PA
authors.lastname: Williams
authors.forename: Kenneth D M
authors.initials: KD
authors.lastname: Harris
authors.forename: Stéphane
authors.initials: S
authors.lastname: Veesler
authors.forename: Hiroki
authors.initials: H
authors.lastname: Takahashi
authors.forename: Hirohito
authors.initials: H
authors.lastname: Tsue
authors.forename: Rui
authors.initials: R
authors.lastname: Tamura
mesh_terms: D001120:Arginine / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D044367:Phase Transition; D013237:Stereoisomerism
chemical_list: D001120:Arginine
keywords: amino acids; chiral resolution; cocrystals; crystal growth; phase transitions