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A kind of hydrophobic quaternary ammonium type biocompatible ionic liquid and its preparation method and application

An ionic liquid and biotransformation technology, which is applied in the preparation of amino compounds, organic compounds, and carboxylate salts, can solve the problems of inhibition, toxicity, and low water solubility of sterol substrates, so as to promote the dissolution of substrates and improve Process conversion efficiency, effectiveness in mitigating product inhibition issues

Active Publication Date: 2020-10-16
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the degradation of phytosterol side chains by mycobacteria to obtain AD requires a 16-step reaction process catalyzed by 11 functional enzymes, which can only be completed in whole cells so far.
There are two main problems: (1) the low water solubility of the sterol substrate; (2) the inhibition or even toxicity of the hydrophobic product AD to the cell activity in the cell, and the inclusion of the substrate particle and the cell after precipitation
[0005] The history of ionic liquid / water two-phase system for whole-cell biocatalysis can be traced back to 2000 (Biotechnology and Bioengineering.2000,69:227-233), but until now, most researches still focus on Screening suitable ionic liquids (mainly imidazole and pyrrolidine ionic liquids) in commercial ionic liquids (Journal of Chemical Technology and Biotechnology.2016,91:2631-2637), few reports have been designed and synthesized for specific biotransformation processes Novel Biocompatible Ionic Liquids

Method used

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  • A kind of hydrophobic quaternary ammonium type biocompatible ionic liquid and its preparation method and application
  • A kind of hydrophobic quaternary ammonium type biocompatible ionic liquid and its preparation method and application
  • A kind of hydrophobic quaternary ammonium type biocompatible ionic liquid and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: tetradecyl ammonium lactate ([N 10,10,10,10 ][Lac]) Synthesis and Characterization of Ionic Liquids

[0027] First prepare [N 10,10,10,10 ][Br] corresponding base [N 10,10,10,10 ][OH]. Specifically, [N 10,10,10,10 ][Br] was dissolved in ethanol to obtain a 30vol.% ethanol solution. Use Dowex Monosphere 550A UPW (OH) strongly basic anion exchange resin (wet volume loading capacity 1.1meq mL -1 ) to fill the exchange column (500×20mm), wash the column with ethanol as the mobile phase for 1h and load the sample at a flow rate of 1mL min -1 . After the ion exchange is completed, use 0.1M HNO 3 +AgNO 3 Solution detection without precipitation indicates that Br - is completely substituted, that is, the corresponding base [N 10,10,10,10 ][OH] in ethanol. Then the ionic liquid was synthesized by neutralization method. Specifically, first calibrate with 0.1M HCl solution (acid-base neutralization titration) [N 10,10,10,10 ] [OH] ethanol solution concen...

Embodiment 2

[0029] Embodiment 2: Tetradecylammonium octanoate ([N 10,10,10,10 ][C 7 h 15 COO]) Synthesis of Ionic Liquids

[0030] Synthesize ionic liquid by the method in embodiment 1 [N 10,10,10,10 ][C 7 h 15 COO], just replacing the lactic acid in the reactant with octanoic acid. The prepared ionic liquid is a transparent liquid at the reaction temperature (45°C), and is solid when the temperature is lowered to room temperature (25°C).

Embodiment 3

[0031] Embodiment 3: ionic liquid [N 10,10,10,10 Basic physicochemical properties of ][Lac]

[0032] At 30°C, the density of the ionic liquid was measured to be 0.90 g cm by the mass-volume method -3 The viscosity of the ionic liquid measured by the NDJ-8S rotational viscometer is 1063cP; the viscosity of the saturated aqueous solution of the ionic liquid is 0.9cP; the hydrophobicity parameter log P of the ionic liquid is 1.6 with octanol-water partition coefficient; Polarity parameter E of ionic liquid measured by probe Reichardt stain N T It was 0.41; the hydrogen bond basicity parameter β of the ionic liquid measured by Kamlet-Taft solvatochrome method was 1.17. When the ionic liquid / water two-phase system reaches the equilibrium state, the solubility of the ionic liquid in water is 0.1wt.%, while the solubility of water in the ionic liquid is 8.6wt.%.

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Abstract

The invention discloses a synthesis method of hydrophobic quaternary ammonium biocompatible ionic liquid and application of the hydrophobic quaternary ammonium biocompatible ionic liquid to the phytosterol whole cell biological conversion process. The ionic liquid is characterized by being prepared rom tetrakisammonium positive ions and lactate or carboxylate radical negative ions. The synthesis process can be completed through simple acid-base neutralization reaction; the operation is simple and convenient; the yield is high. The obtained ionic liquid has high hydrophobic performance, weak polarity and strong hydrogen bonding alkalinity, so that the excellent dissolution and extraction performance is shown on sterol; good biocompatibility is realized; the influence on the glucose metabolic activity of microbial cells is small; an ionic liquid / buffer liquid two-phase biological conversion system can be built and is used for mycobacteria catalyzed phytosterol side chain degradation process; the substrate dissolution is promoted; meanwhile, the in-situ extraction of products can be realized; the process conversion efficiency is improved.

Description

technical field [0001] The invention relates to a hydrophobic quaternary ammonium type biocompatible ionic liquid and its preparation method and application, especially the application in the whole cell biotransformation process of phytosterol. Background technique [0002] Androst-4-ene-3,17-dione (AD) is an important steroid drug intermediate, which can be used to synthesize hundreds of steroid hormone drugs. Using abundant phytosterols in nature as substrates, the preparation of AD by biotransformation has broad application prospects. However, the degradation of phytosterol side chains by mycobacteria to obtain AD requires a 16-step reaction process catalyzed by 11 functional enzymes, which can only be completed in whole cells so far. There are two main problems: (1) the low water solubility of the sterol substrate; (2) the inhibition and even toxicity of the hydrophobic product AD to the cell activity in the cell, and the inclusion of the substrate particles and cells a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/41C07C59/08C07C53/126C07C211/63C07C209/00C07C209/68C07C209/74C12P33/16
CPCC07C53/126C07C59/08C07C211/63C12P33/16
Inventor 关怡新袁俊杰肖霞姚善泾
Owner ZHEJIANG UNIV
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