Highly Efficient Chiral Resolution of dl‐Arginine by Cocrystal Formation Followed by Recrystallization under Preferential‐Enrichment Conditions |
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| Authors: | Dr Sekai Iwama Kazunori Kuyama Yuko Mori Dr Kochunnoonny Manoj Dr Rajesh G Gonnade Dr Katsuaki Suzuki Dr Colan E Hughes P Andrew Williams Prof Kenneth D M Harris Dr Stéphane Veesler Dr Hiroki Takahashi Prof Hirohito Tsue Prof Rui Tamura |
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| Institution: | 1. Graduate School of Human and Environmental Studies, Kyoto University, Yoshida Nihonmatsu‐cho, Sakyo‐ku, Kyoto 606‐8501 (Japan), Fax: (+81)?75‐753‐7915;2. Centre for Materials Characterization, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008 (India);3. School of Chemistry, Cardiff University, Park Place, Cardiff CF10?3AT (UK);4. Centre Interdisciplinaire de Nanoscience de Marseille, CINAM‐CNRS, Aix‐Marseille Université, Campus de Luminy, Case 913, 13288 Marseille CEDEX 09 (France) |
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| 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 13C NMR spectroscopic studies on the crystallization process, a new mechanism of phase transition that can induce preferential enrichment is proposed. |
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| Keywords: | amino acids chiral resolution cocrystals crystal growth phase transitions |
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