Amino-protecting serine oligopeptide as well as preparation method and application thereof

An amino-protected and serine technology, applied in the field of amino acid modification compounds, can solve the problem of no amino-protected serine oligopeptide, etc., and achieve the effects of improving yield and purity and reducing the generation of impurities

Inactive Publication Date: 2011-12-07
CHENGDU SHENGNUO BIOTEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, there are only serine and protected serine, and there are no related reports on amino-protected serine oligopeptides

Method used

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  • Amino-protecting serine oligopeptide as well as preparation method and application thereof
  • Amino-protecting serine oligopeptide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The synthesis of embodiment 1Fmoc-Ser(tBu)-Ser(tBu)-Ser(tBu)-Ser(tBu)-OH

[0024] Take 3.0mol Ser(tBu) and 3.0mol HOBt, and dissolve them with an appropriate amount of DMF; take another 3.0mol DIC (N,N-diisopropylcarbodiimide), slowly add it to the protected amino acid DMF solution under stirring, and Stir the reaction at room temperature for 30 minutes to obtain the activated protected amino acid solution.

[0025] Take 1Kg of Fmoc-Ser(tBu)-2-Cl-Trt-resin (substitution value is 1.0mmol / g); use 6L PIP / DMF solution to deprotect for 25 minutes, wherein the volume concentration of PIP is 20%. After filtering, the resin was washed 3 times with MDF and DCM respectively, and the above-mentioned protected amino acid solution was added, and the reaction was stirred at room temperature for 3 hours. After the reaction was completed, the filtered resin was washed 3 times with MDF and DCM respectively to obtain Fmoc-Ser(tBu)-Ser( tBu)-OH.

[0026] The above reaction was repeated ...

Embodiment 2

[0028] Example 2 Application of Fmoc-Ser(tBu)-Ser(tBu)-Ser(tBu)-Ser(tBu)-OH in Polypeptide Synthesis

[0029] Take Fmoc-Lys(Boc)-2-Cl-Trt-resin, after Fmoc deprotection, couple with Fmoc-Ser(tBu)-Ser(tBu)-Ser(tBu)-Ser(tBu)-OH to prepare 5-peptide resin was obtained.

[0030] The coupling method is specifically:

[0031] 1. Activation of Fmoc-Ser(tBu)-Ser(tBu)-Ser(tBu)-Ser(tBu)-OH:

[0032] Take 0.3mol Fmoc-Ser(tBu)-Ser(tBu)-Ser(tBu)-Ser(tBu)-OH and 0.3mol HOBt, and dissolve them with an appropriate amount of DMF; take another 0.3mol DIC, slowly add to the aforementioned DMF under stirring solution, stirred and reacted at room temperature for 30 minutes to obtain an activated protected amino acid solution.

[0033] 2. De-Fmoc protection of Fmoc-Lys(Boc)-2-Cl-Trt-resin:

[0034] Take 200 g of Fmoc-Lys(Boc)-2-Cl-Trt-resin (substitution value: 0.5 mmol / g), use 1 L of 20% PIP / DMF solution to deprotect for 25 minutes, filter and wash with DMF for 5 times to obtain de-Fmoc resin...

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Abstract

The invention belongs to the technical field of amino acid modified compounds, in particular relates to amino-protecting serine oligopeptide as well as a preparation method and application thereof. The structure of amino-protecting serine oligopeptide is shown in a formula I, wherein X is tBu or Trt, and n is 1-4. According to the amino-protecting serine oligopeptide, a novel polypeptide segment is provided for synthesis of polypeptide medicaments, thus impurities are reduced when the polypeptide is synthesized, and the yield and purity are improved.

Description

technical field [0001] The invention belongs to the technical field of amino acid modification compounds, and in particular relates to amino-protected serine oligopeptides and their preparation methods and uses. technical background [0002] Peptide drugs are biologically active substances, and most of them participate in many important physiological processes of the human body, such as hematopoiesis, inhibition of tumor cell activity, immunity, etc. [0003] The research and development of peptide drugs has always been a hot spot in the biopharmaceutical industry. During the preparation of peptides, repeated amino acid sequences are often encountered, resulting in incomplete coupling, which greatly reduces the preparation yield and reduces the preparation cost at the same time. Greatly improved, the patent of the present invention overcomes the above-mentioned problems by preparing protected amino acid oligopeptides, and has a good application prospect. [0004] In the pri...

Claims

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Application Information

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IPC IPC(8): C07K5/072C07K5/093C07K5/113C07K7/06C07K1/06C07K1/04
Inventor 文永均王晓莉叶仲林童光彬
Owner CHENGDU SHENGNUO BIOTEC CO LTD
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