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Synthesis method of cysteine pseudoproline dipeptide

A pseudoproline dipeptide, a technology for a synthesis method, which is applied to the preparation methods of peptides, chemical instruments and methods, peptides, etc., can solve the problems of troublesome post-processing, cumbersome purification, low yield and the like, and achieves efficient and convenient production. Simplify reaction steps, reduce the effect of reaction steps

Inactive Publication Date: 2019-06-04
GL BIOCHEM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It not only solves the technical problems of low yield, tedious and difficult purification, and troublesome post-processing of the existing synthetic methods; it also solves the problem that (X : Gly, Phe, Val, Ile, Leu, Pro, Ala, Met and other amino acids) It is necessary to repeat the production process to synthesize different Fmoc-X-Cys-OH, making the production more efficient and simple

Method used

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  • Synthesis method of cysteine pseudoproline dipeptide
  • Synthesis method of cysteine pseudoproline dipeptide
  • Synthesis method of cysteine pseudoproline dipeptide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step 1 synthetic route:

[0030]

[0031] In a 5L three-neck flask, add Cys-OH.Hcl 94.6g (0.6mol), add 2,2-dimethoxypropane 624g (6.0mol), add 3.5L acetone and stir, heat to reflux for 1hr, cool to room temperature, and filter with suction , the filter cake was washed twice with acetone,

[0032] Dry to obtain Cys[Psi(Me,Me)Pro]-OH 84.1g. (Theoretical yield is 96.6g), the yield is 87.0%, and the HPLC purity is 96.8%.

[0033] Step 2 synthetic route:

[0034]

[0035] In a 2L three-necked flask, add 59g (0.2mol) of Fmoc-Gly-OH, add 800ml THF, stir to dissolve, and cool down to

[0036] Add 40.7g (0.24mol) of DAST at 0°C, add 40.7g (0.24mol) in 15 minutes, rise to room temperature and react for 1 hour, pour into 800ml of ice water, extract the product with ethyl acetate, wash the organic phase twice with water, twice with brine, anhydrous sulfuric acid Sodium dried, filtered,

[0037] The filtrate was precipitated until solids were precipitated, filtered, and d...

Embodiment 2

[0045] The Fmoc-Gly-OH in step 2 can also be extended to other Fmoc-protected amino acids to perform the same reaction.

[0046] Gly can be replaced by other amino acids such as Phe, Val, Ile, Leu, Pro, Ala, Met; the rest refer to Example 1.

Embodiment 3

[0048] The organic base DIEA used in step 3 can be replaced by triethylamine, and the reaction is carried out to obtain the final product Fmoc-Gly-Cys[Psi(Me,Me)Pro]-OH); the rest refer to Example 1.

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Abstract

The invention relates to a synthesis method of cysteine pseudoproline dipeptide. The invention mainly solves the technical problems of low dipeptide yield, difficult purity improvement, complicated post-treatment steps and long production period of synthesis methods in the prior art. The technical solution of the invention is as follows: the synthesis method of the cysteine pseudoproline dipeptidecomprises the following steps: step 1, placing H-Cys-OH.HCl in acetone, adding 2,2-dimethoxypropane, and performing reflux to obtain a common intermediate Cys[Psi(Me, Me)Pro]-OH; step 2, subjecting Fmoc-X-OH and DAST to reaction in a THF solution to obtain Fmoc-X-F; and step 3, placing the Cys[Psi(Me, Me)Pro]-OH and the Fmoc-X-F in DMF, adding organic base for condensation, and performing processing to obtain a final product Fmoc-X-Cys[Psi(Me, Me)Pro]-OH. The X is selected from one of Gly, Phe, Val, Ile, Leu, Pro, Ala or Met.

Description

technical field [0001] The invention relates to a synthetic method of pseudoproline dipeptide, in particular to a synthetic method of cysteine ​​pseudoproline dipeptide. Background technique [0002] The structural formula of cysteine ​​pseudoproline dipeptide (Fmoc-X-Cys[Psi(Me,Me)Pro]-OH) is: [0003] [0004] Pseudoproline dipeptides can be used as reversible protecting groups for Ser, Thr, and Cys, and are therefore versatile tools in chemistry. The traditional method (refer to Patent Publication No. CN101472939A) obtains Fmoc-X-Cys by direct cyclization of dipeptide Fmoc-X-Cys-OH (X: Gly, Phe, Val, Ile, Leu, Pro, Ala, Met and other amino acids) [Psi(Me,Me)Pro]-OH, the literature method has the following technical problems in the actual synthesis process: [0005] 1. In the process of synthesizing dipeptide Fmoc-X-Cys-OH, the yield of dipeptide is low and the purity is not easy to improve; [0006] 2. The reaction is not complete during the ring formation reaction,...

Claims

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Application Information

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IPC IPC(8): C07K5/072C07K1/30C07K1/06
Inventor 徐红岩彭瑞涛周国峰林崔健
Owner GL BIOCHEM SHANGHAI
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