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New method for separation of phenylalanine enantiomer by reaction extraction

A technology of phenylalanine and enantiomers, which is applied in the field of separation of phenylalanine enantiomers in the reaction extraction process, can solve the problem of low selectivity for separating amino acid enantiomers, achieve good reusability and reduce production costs , cheap effect

Inactive Publication Date: 2012-10-03
唐课文 +1
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Problems solved by technology

[0005] This patent proposes a new chiral extraction method for the low selectivity of amino acid enantiomers in the extraction and separation of general chiral extractants: based on chiral Chiral Extraction Technique of BINAP (2,2'-Bisdiphenylphosphine-1,1'-binaphthyl)-Metal Complexes

Method used

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  • New method for separation of phenylalanine enantiomer by reaction extraction

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Embodiment 1

[0011] D,L - Phenylalanine dissolved in 0.1 mmol / L NaH 2 PO 4 / Na 2 HPO 4 Buffer solution and adjust pH = 5.0 ~ 9.0, control D,L - The concentration of phenylalanine is 2~10 mmol / L to obtain the aqueous phase. Chirality ( S )-BINAP and tetraacetonitrile copper hexafluorophosphate ( ), diacetonitrile palladium dichloride and bis(triphenylphosphine) nickel chloride ( ) was dissolved in 1,2-dichloroethane according to the proportion, fully stirred, and controlled ( S )-BINAP and the molar ratio of the aforementioned three metal ions are 0.5 ~ 5, and make ( S )-BINAP concentration was controlled within the concentration range of 1-5 mmol / L to obtain an organic phase. Take 10 mL each of the aqueous phase and the organic phase and put them into test tubes, shake in a constant temperature shaker in a water bath for 9 to 14 hours, and control the constant temperature within the range of 5 to 30 °C. Thereafter, the two phases were kept at constant temperature for more tha...

Embodiment 2

[0013] Tetraacetonitrile copper hexafluorophosphate ( ) as the central ion donor of the extractant, and chiral ( S )-BINAP undergoes complexation reaction in 1,2-dichloroethane to obtain ( S )-BINAP-Copper( ) complex solution, the control solution ( S )-BINAP concentration is 10mmol / L. D,L-phenylalanine dissolved in 0.1mom / L NaH 2 PO 4 / Na 2 HPO 4 Adjust pH = 9.0 in buffer solution, control D,L - The concentration of phenylalanine is 20 mmol / L. An organic phase and an aqueous phase were obtained respectively through the above two steps of operation. Take 50 mL of the organic phase and 50 mL of the aqueous phase in a 250 mL separatory funnel for extraction operation, mix well and let the two phases reach equilibrium. Measure the concentration of phenylalanine enantiomer in organic phase and aqueous phase respectively, and carry out material constant calculation, determine D and L - the partition coefficient of the enantiomer ( k D and k L ) were 0.101 and 0....

Embodiment 3

[0015] Tetraacetonitrile copper hexafluorophosphate ( ) as the central ion donor of the extractant, and chiral ( S )-BINAP undergoes complexation reaction in 1,2-dichloroethane to obtain ( S )-BINAP-Copper( ) complex solution, the control solution ( S )-BINAP with copper ( ) ion concentration is 2 mmol / L. D,L-phenylalanine dissolved in 0.1 mol / L NaH 2 PO 4 / Na 2 HPO 4 buffer solution and adjust to pH = 9.0. Prepare D, L-phenylalanine concentration of 1, 2, 3, 4 mmol / L four groups of aqueous phase solutions. Take 10 mL of the organic phase obtained above and put 10 mL of each of the four groups of water phases into different test tubes, and perform the extraction operation in a constant temperature shaker in a water bath (the constant temperature is controlled at 5°C). Mix well and let stand to separate the layers, so that the two phases reach equilibrium, then detect the extraction effect. The results showed that the partition coefficients of the enantiomers of t...

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Abstract

The invention discloses a new method for separation of phenylalanine enantiomer by reaction extraction, which uses (S)-BINAP-copper complex as chiral extractant in the organic phase to extract and separate phenylalanine enantiomer from the water phase. The invention discloses a preparation method for (S)-BINAP-copper complex. (S)-BINAP-copper complex has good complexing capability and high enantiomer selectivity to phenylalanine enantiomer, and the separation factor alpha is up to over 5.0.

Description

technical field [0001] The invention relates to a method for extracting and separating the enantiomers of phenylalanine, specifically ( S )-BINAP (2,2'-bisdiphenylphosphine-1,1'-binaphthyl)-metal copper complex as a chiral extractant, a method for separating phenylalanine enantiomers through a reaction extraction process. Background technique [0002] α -Amino acid is a class of small molecular compounds that widely exist in nature. It has the function of preventing and curing diseases in medicine, especially the optically active amino acid has important biological activity and physiological function. An important precursor of a series of peptides. Phenylalanine is an aromatic amino acid with physiological activity. As one of the eight essential amino acids for human body, it is widely used in medicine and food industry. D -Phenylalanine can enhance the immune function of the human body and has excellent analgesic effect. L-phenylalanine is an important component of comp...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/34
Inventor 唐课文张盼良吴国辉刘永兵周从山杨长安易健民
Owner 唐课文
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