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Lysine alpha-amino carbobenzoxy high-efficiency selective protection method and product thereof

A technology of benzyloxycarbonyl and lysine, applied in the field of efficient and selective protection of benzyloxycarbonyl, can solve the problems of multiple environmental pollutants, high treatment cost, harsh conditions, etc. Effect

Inactive Publication Date: 2012-07-18
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In general, the existing selective protection method for lysine α-amino group has harsh conditions, long time, low yield, high cost, more environmental pollutants, and high processing cost

Method used

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  • Lysine alpha-amino carbobenzoxy high-efficiency selective protection method and product thereof
  • Lysine alpha-amino carbobenzoxy high-efficiency selective protection method and product thereof
  • Lysine alpha-amino carbobenzoxy high-efficiency selective protection method and product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 11.35 g of β-cyclodextrin was dissolved in 113.5 g of purified water and adjusted to pH=8.5 with carbonate. 14.6 g of lysine were added to the above aqueous solution at 20°C. After the lysine is completely dissolved, add dropwise the benzyl chloroformate with a molar ratio of lysine:benzyl chloroformate=1:1.1 under the temperature control of the system at 19-21°C, and continue stirring for 10 minutes. The reaction solution was adjusted to pH=6.9 with hydrochloric acid, and extracted three times with 330 mL of ethyl acetate. The extracts were combined, and the solvent was distilled under the conditions of 30°C and 25mmHg pressure to obtain the lysine α-amino Cbz pre-protected product.

[0036] Physical and chemical data of the above product: melting point m.p.229℃~230℃ (literature value: m.p.227℃~231℃); mass spectrum (C 14 h 20 N 2 o 4 ): ESI-MS: 281.1 [M+H + ]; 303.1 [M+Na + ]; liquid chromatography-mass spectrometry data as shown in the figure (mobile phase: meth...

Embodiment 2

[0038] (1) In parts by weight (unit: kilogram), dissolve 30 parts of β-cyclodextrin in 100 parts of water, and adjust the pH to 8.5 with sodium hydroxide solution;

[0039] (2) Add lysine to the above solution at a molar ratio of β-cyclodextrin: lysine = 1:10 at 25°C, and stir until the lysine is completely dissolved;

[0040] (3) Add benzyl chloroformate dropwise to the solution of step (2) in a molar ratio of lysine: benzyl chloroformate=1:1.5, while controlling the reaction temperature at 20 ± 1°C, and continue stirring 20 minutes;

[0041] (4) the reaction solution is adjusted to neutrality with hydrochloric acid;

[0042] (5) step (4) solution is extracted 5 times with ethyl acetate;

[0043] (6) Combine the extracts, distill under reduced pressure at a temperature of 30° C. and a pressure of 25 mmHg to obtain the benzyloxycarbonyl pre-protected product of the α-amino group of lysine.

Embodiment 3

[0045] (1) In parts by weight (unit: kilogram), 40 parts of β-cyclodextrin was dissolved in 100 parts of water, and adjusted to pH=8.0 with sodium hydroxide solution;

[0046] (2) Add lysine into the above solution at a molar ratio of β-cyclodextrin: lysine = 1:50 at 22°C, and stir until the lysine is completely dissolved;

[0047] (3) Add benzyl chloroformate dropwise to the solution of step (2) in a molar ratio of lysine: benzyl chloroformate=1:50, while controlling the reaction temperature at 20 ± 1°C, and continue stirring 60 minutes;

[0048] (4) the reaction solution is adjusted to neutrality with hydrochloric acid;

[0049] (5) step (4) solution is extracted 5 times with ethyl acetate;

[0050](6) Combine the extracts, distill under reduced pressure at a temperature of 30° C. and a pressure of 25 mmHg to obtain the benzyloxycarbonyl pre-protected product of the α-amino group of lysine.

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Abstract

The invention discloses a lysine alpha-amino carbobenzoxy high-efficiency selective protection method, which enables beta-cyclodextrin to be dissolved in water and uses alkali to adjust to alkalescence, adds in lysine for blending and dissolving, drops in benzyl chloroformate, simultaneously controls reaction temperature at 18-23 DEG C, continuously blends to obtain reaction liquid, extracts the reaction liquid by using organic solvent, combines extraction liquid, conducts decompression and distillation to obtain lysine alpha-amino carbobenzoxy pre-protection products. The lysine alpha-amino carbobenzoxy high-efficiency selective protection method is simple and convenient, practical, high in yield, low in cost, small in investment, free of the three wastes discharge, and particularly applicable to production of medium-sized and small enterprises.

Description

technical field [0001] The invention relates to a high-efficiency and selective protection method for benzyloxycarbonyl (Cbz) of lysine α-amino group and a product thereof, belonging to the field of fine chemical industry. Background technique [0002] Lysine is the basic unit of protein and the main raw material for the synthesis of human hormones, enzymes and antibodies. In recent years, lysine and its derivatives have been widely used in the artificial synthesis of peptides and proteins, and have great potential in the fields of synthetic drug carriers, drug intermediates, new functional materials, and biomacromolecular simulations. However, in the process of synthesizing lysine derivatives, it is usually required that the α-amino and ε-amino groups of lysine are connected to peptides of different sequences, which requires selective protection of different amino groups of lysine, that is, a While an amino group is protected by a protecting group, the other amino group is...

Claims

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Application Information

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IPC IPC(8): C07C271/22C07C269/04
Inventor 李尚洋苏杰郝爱友
Owner SHANDONG UNIV
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