New Optical Resolution Method for Racemic DL-Aspartic Acid by Crystallization in the Presence of D- or L-Asparagine as a Tailor-Made Additive

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  • Sato Hiroyasu
    Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University Chemical Technology Laboratory, Taiho Pharmaceutical Co., Ltd.
  • Doki Norihito
    Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University
  • Yokota Masaaki
    Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University
  • Shimizu Kenji
    Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University
  • Yano Shingo
    Chemical Technology Laboratory, Taiho Pharmaceutical Co., Ltd.

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  • New Optical Resolution Method for Racemic <small>DL</small>-Aspartic Acid by Crystallization in the Presence of d- or l-Asparagine as a Tailor-Made Additive

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A new optical resolution method is proposed in which one enantiomer of a racemic mixture is replaced with a tailor-made additive, and the displaced enantiomer is crystallized. DL-Aspartic acid (Asp) was examined as a model racemic compound. First, L-Asp crystallization was examined in the presence of L-asparagine (Asn) or D-Asn. The effect of Asn was chirality-specific; L-Asn specifically replaced some of the L-Asp in the crystal lattice and solid solutions of L-Asp with L-Asn formed. Secondly, DL-Asp crystallization was examined in the presence of L-Asn, and the obtained crystals were solid solutions of DL-Asp with L-Asn partially replacing L-Asp in the DL-Asp crystal lattice. Finally, crystallization of the L-Asp in the filtrate of the DL-Asp crystallization in the presence of L-Asn was examined. The obtained crystals were a mixture of solid solutions of L-Asp with L-Asn and solid solutions of DL-Asp with L-Asn. Moreover, when D-Asn was added to the DL-Asp crystallization, a mixture of solid solutions of D-Asp with D-Asn and solid solutions of DL-Asp with D-Asn was crystallized from the filtrate. These results show that racemic compounds could be resolved by the proposed method.

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