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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- Sato Hiroyasu
- Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University Chemical Technology Laboratory, Taiho Pharmaceutical Co., Ltd.
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- Doki Norihito
- Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University
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- Yokota Masaaki
- Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University
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- Shimizu Kenji
- Department of Chemistry and Bioengineering, Faculty of Engineering, Iwate University
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- Yano Shingo
- Chemical Technology Laboratory, Taiho Pharmaceutical Co., Ltd.
Bibliographic Information
- Other Title
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- 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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Abstract
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.
Journal
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- JOURNAL OF CHEMICAL ENGINEERING OF JAPAN
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JOURNAL OF CHEMICAL ENGINEERING OF JAPAN 48 (11), 903-908, 2015
The Society of Chemical Engineers, Japan
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Details 詳細情報について
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- CRID
- 1390001204568763136
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- NII Article ID
- 130005110446
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- NII Book ID
- AA00709658
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- ISSN
- 18811299
- 00219592
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- NDL BIB ID
- 027013685
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed