Highly efficient chiral resolution of DL-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions

Sekai Iwama; Kazunori Kuyama; Yuko Mori; Kochunnoonny Manoj; Rajesh G Gonnade; Katsuaki Suzuki; Colan E Hughes; P Andrew Williams; Kenneth D M Harris; Stéphane Veesler; Hiroki Takahashi; Hirohito Tsue; Rui Tamura

doi:10.1002/chem.201402446

Highly efficient chiral resolution of DL-arginine by cocrystal formation followed by recrystallization under preferential-enrichment conditions

Chemistry. 2014 Aug 11;20(33):10343-50. doi: 10.1002/chem.201402446. Epub 2014 Jul 15.

Authors

Sekai Iwama¹, Kazunori Kuyama, Yuko Mori, Kochunnoonny Manoj, Rajesh G Gonnade, Katsuaki Suzuki, Colan E Hughes, P Andrew Williams, Kenneth D M Harris, Stéphane Veesler, Hiroki Takahashi, Hirohito Tsue, Rui Tamura

Affiliation

¹ Graduate School of Human and Environmental Studies, Kyoto University, Yoshida Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501 (Japan), Fax: (+81) 75-753-7915.

PMID: 25042834
DOI: 10.1002/chem.201402446

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.

Keywords: amino acids; chiral resolution; cocrystals; crystal growth; phase transitions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Arginine / chemistry*
Crystallization
Crystallography, X-Ray
Models, Molecular
Phase Transition
Stereoisomerism

Substances

Arginine