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Chiral extraction of amino acid enantiomers using (S)-SEGPHOS-metal complexes as extractants

Xiong Liu, Yu Ma, Ting Cao, Su-ping Jiang, and Pei-yi Yang

School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, People’s Republic of China

 

E-mail: liuxiongcsu@163.com

Received: 5 September 2019  Accepted: 19 October 2019

Abstract:

In this study, (S)-SEGPHOS was adopted as chiral extractant to recognize amino acid enantiomers. Phenylalanine (Pha), homophenylalanine (Hpha), 4-nitro-phenylalanine (Npha), phenylglycine (Phg), 3-chloro-phenylglycine (Cphg), and tyrosine (Tys) were selected as substrates to estimate the enantioselectivities of (S)-SEGPHOS-metal complexes. (S)-SEGPHOS-Pd was an excellent chiral extractant to recognize Npha with operational enantioselectivity (α) was 4.25. And (S)-SEGPHOS-Cu was a good chiral extractant to recognize Pha, Hpha, Phg, Tys, and Cphg with α were 2.87, 1.93, 2.28, 4.07, and 2.94, respectively. After optimization by response surface methodology, the highest performance factors (pf) for Pha, Hpha, Phg, Npha, Tys, and Cphg were 0.22893, 0.11085, 0.14003, 0.25476, 0.21414, and 0.23142, respectively. Based on experimental results, the possible recognize mechanisms were discussed.

Keywords: (S)-SEGPHOS-metal complexes; Chiral extraction; Amino acid enantiomers; Response surface methodology; Recognize mechanism

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-019-00970-z

 

Chemical Papers 74 (4) 1229–1239 (2020)

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