Method of resolving optical isomers of amino acid derivative

Details Method of resolving optical isomers of amino acid derivative Method of resolving optical isomers of amino acid derivative

2007-04-03

2007-04-03

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

Reexamination Certificate

active

10415559

ABSTRACT:
Provided is a separating method for an optical isomer mixture comprising the steps of mixing an amino acid derivative such as N-(tert-butoxycarbonyl)-DL-alanine in which optical isomers of a D type and an L type are present in a mixture with a hydrophilic compound such as β-cyclodextrin having a different affinity to two kinds of the optical isomers described above and then bringing the resulting aqueous solution or aqueous suspension into contact with a hydrophobic substance such as a solid matter subjected on a surface thereof to hydrophobic treatment on the condition that the pH is 3.5 or lower or under the coexistence of ions including an atomic group having hydrophobicity which can be a counter ion for the amino acid derivative described above such as a triethylammonium ion to thereby separate the D type amino acid derivative from the L type amino acid derivative present in the above aqueous solution or aqueous suspension.

REFERENCES:
patent: 5578212 (1996-11-01), Pirkle et al.
Li et al., Journal of Chromatography, 1992, 625: 109-120.
S. Li et al., “Direct separation of enantiomers using multiple-interaction chiral stationary phases based on the modified β-cyclodextrin-bonded stationary phase”, Journal of Chromatography, vol. 625, No. 2, pp. 109-120, 1992.
T. Takeuchi et al., “Enantiomeric Resolution of Dansyl Amino Acids by Micro High-Performance Liquid Chromatography with β-Cyclo-Dextrin Inclusion Complexes ”, Journal of Chromatography, vol. 357, pp. 409-415, 1986.
S. C. Chang et al., “Facile Resolution of N-tert-Butoxy-Carbonyl Amino Acids: The Importance of Enantiomeric Purity in Peptide Synthesis”, Journal of Liquid Chromatography, vol. 15, No. 9, pp. 1411-1429, 1992.
C. Pettersson, “Chromatographic Separation of Enantiomers of Acids with Quinine as Chiral Counter Ion”, Journal of Chromatography, vol. 316, pp. 553-567, 1984.
S. C. Chang et al., “Facile Resolution of N-tert-Butoxy-Carbonyl Amino Acids:” The Importance of Enantiomeric Purity in Peptide Synthesis, Journal of Liquid Chromatography, 1992, vol. 15, No. 9, pp. 1411-1429, especially pp. 1423 and 1424.

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