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Nalpha-fluorenylmethyloxycarbonyl-Nepsilon-trifluoroacetyl-lysine preparation method

The technology of fluorene methoxycarbonyl and trifluoroacetyl is applied in the field of preparation of lysine, can solve problems such as difficulty in production and operation, and achieve the effects of stable and reliable product quality, avoiding difficult washing and reducing costs

Active Publication Date: 2013-10-02
GL BIOCHEM SHANGHAI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a preparation method of Nα-fluorenylmethoxycarbonyl-Nε-trifluoroacetyl-lysine, which mainly solves the technical problem of difficult production and operation in the existing synthesis method

Method used

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  • Nalpha-fluorenylmethyloxycarbonyl-Nepsilon-trifluoroacetyl-lysine preparation method

Examples

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Effect test

Embodiment 1

[0019] Example 1: Dissolve 1 equivalent of Nα-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysine in dichloromethane, add 1 part of a dichloromethane solution with a mass percentage of 15% trifluoroacetic acid, Stir vigorously, cool with tap water externally, detect the reaction is complete by thin-layer chromatography, distill off the solvent and trifluoroacetic acid under reduced pressure, wash with petroleum ether, pour off the petroleum ether and dissolve in tetrahydrofuran, add N-methylmorpholine until the pH is weakly alkaline ( 7﹤pH≤8, the same as below) and stir; take another bottle, add trifluoroacetic acid and dimethylformamide to it, stir in the peripheral ice bath, add thionyl chloride dropwise, generate gas and pass into Nα-fluorenylmethoxycarbonyl - In L-lysine tetrahydrofuran solution, after the dropwise addition, nitrogen gas is blown into the gas generating container, so that the generated gas further enters the following reaction, the progress of the re...

Embodiment 2

[0020] Example 2: Dissolve 1 equivalent of Nα-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysine in ethanol or ether, pass in hydrogen chloride gas, stir vigorously, cool the outside with tap water, and check that the reaction is complete by thin-layer chromatography. Filter off the solvent, wash with ether, dissolve in tetrahydrofuran, add N,N-diisopropylethylamine until the pH is weakly alkaline and stir; take another bottle, add trifluoroacetic acid and dimethylformamide to it, stir, and ice Bath, add thionyl chloride dropwise, the generated gas is passed into the Nα-fluorenylmethoxycarbonyl-L-lysine tetrahydrofuran solution, after the dropwise addition, nitrogen is blown into the gas generating container, so that the generated gas further enters the following reaction , thin-layer chromatography to detect the reaction progress, pH test paper to detect the acidity of the reaction system, and maintain the pH value at 10. After the reaction, concentrate the reaction so...

Embodiment 3

[0021] Example 3: 1 equivalent of Nα-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-D-lysine was dissolved in dichloromethane, and 3 parts of trifluoroacetic acid in dichloromethane with a mass percent content of 35% were added, Vigorously stir, cool with tap water externally, complete reaction by TLC, distill off solvent and trifluoroacetic acid under reduced pressure, wash with petroleum ether, pour off petroleum ether and dissolve in tetrahydrofuran, add N-methylmorpholine until the pH is weakly alkaline and stir ; Take another bottle, add trifluoroacetic acid and dimethylformamide to it, stir in the peripheral ice bath, add thionyl chloride dropwise, generate gas and pass it into the Nα-fluorenylmethoxycarbonyl-D-lysine tetrahydrofuran solution, After the dropwise addition is completed, nitrogen is blown into the gas generating container so that the generated gas further enters the following reaction, the reaction progress is detected by thin layer chromatography, and th...

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Abstract

The invention relates to a Nalpha-fluorenylmethyloxycarbonyl-Nepsilon-trifluoroacetyl-lysine preparation method, wherein a purpose of the present invention is mainly to solve a technical problem of large production operation difficulty in the existing synthesis method. The technical scheme comprises that the Nalpha-fluorenylmethyloxycarbonyl-Nepsilon-trifluoroacetyl-lysine preparation method comprises the following steps: adopting Nalpha-fluorenylmethyloxycarbonyl-Nepsilon-tertbutyloxycarbonyl-lysine as a starting material, carrying out tertbutyloxycarbonyl removal, purifying Nalpha-fluorenylmethyloxycarbonyl-lysine, carrying out a reaction of the purified Nalpha-fluorenylmethyloxycarbonyl-lysine and trifluoroacetyl chloride to obtain the Nalpha-fluorenylmethyloxycarbonyl-Nepsilon-trifluoroacetyl-lysine, and carrying out a purification treatment to obtain the product, wherein the product is used in the field of polypeptide synthesis.

Description

technical field [0001] The invention relates to a preparation method of lysine, especially a preparation method of Nα-fluorenylmethoxycarbonyl-Nε-trifluoroacetyl-lysine. Background technique [0002] Nα-fluorenylmethoxycarbonyl-Nε-trifluoroacetyl-lysine is a commonly used amino acid protection reagent, which is often used in the field of peptide synthesis. In the previous production process, metals such as copper salt were used to chelate the α-amino group and carboxyl group of lysine, and then the side chain amino group was reacted with trifluoroacetyl chloride under alkaline conditions, and then ethylenediaminetetraacetic acid or its Decopper the sodium salt, then purify the product, and react the purified product with fluorenylmethoxycarbonyl succinimide to obtain the product; in fact, this route is quite difficult to produce, first, Nε-trifluoroacetyl-lysine The acid is extremely hydrophilic and difficult to extract and purify; second, it is not easy to handle after the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/22C07C269/06
Inventor 徐红岩李忠亮
Owner GL BIOCHEM SHANGHAI
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