Novel aspartic acid derivative, preparation method and use thereof in solid-phase polypeptide synthesis

A technology of aspartic acid and derivatives, which is applied in the preparation of carbamic acid derivatives, organic compounds, hydrogenated polysulfides/polysulfides, etc., which can solve the problems of expensive additives, low efficiency of Fmoc removal, and effect effects Larger issues

Inactive Publication Date: 2016-11-30
PEKING UNIV
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Problems solved by technology

These methods have achieved good results for the synthesis of some polypeptides, but at the same time there are also difficulties in deprotection, expensive additives, low efficiency of Fmoc removal, difficulty in preparing corresponding aspartic acid derivatives and easy decomposition, and the effect is affected by the amino acid sequence. Large impact and other limitations

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  • Novel aspartic acid derivative, preparation method and use thereof in solid-phase polypeptide synthesis
  • Novel aspartic acid derivative, preparation method and use thereof in solid-phase polypeptide synthesis
  • Novel aspartic acid derivative, preparation method and use thereof in solid-phase polypeptide synthesis

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Embodiment Construction

[0020]

[0021] (1) Synthesis of compound 5: Dissolve compound 1 (1g, 3mmol) in N,N-dimethylformamide (10ml), add N,N-diisopropylethylamine (0.8ml, 4.5mmol) and propenyl bromide (0.34ml, 4.44mmol). The reaction was stirred overnight at room temperature, and the reaction was monitored by thin-layer chromatography. After the reaction was completed, acid was added to terminate the reaction. Add ethyl acetate to dilute the reaction, wash the organic layer with water and saturated brine respectively, dry the organic phase with anhydrous magnesium sulfate, filter with suction, spin dry and pass through a silica gel column, the eluent is petroleum ether:ethyl acetate (9:1 ), finally obtained a colorless oil with a yield of 95%. 1 H NMR (400MHz, CDCl3) δ5.87 (dddd, J = 5.3, 5.6, 10.2, 16.9Hz, 1H), 5.48 (br d, J = 8.4Hz, 1H), 5.31 (dq, J = 16.8, 1.5Hz ,1H),5.22(dq,J=10.5,1.1Hz,1H),4.65(ddt,J=13.0,5.5,1.5Hz,1H),4.63(ddt,J=13.4,

[0022] 5.7,1.5Hz,1H),4.54(dt,J=4.5,8.8Hz,1H),2.92(d...

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Abstract

The invention relates to a novel aspartic acid derivative, a preparation method and use thereof in solid-phase polypeptide synthesis. During solid-phase polypeptide synthesis, the beta site group on the aspartic acid derivative has the effect of inhibiting the derivative from forming aspartimide.

Description

technical field [0001] The method relates to the modification of aspartic acid, a method for inhibiting the formation of asparagine. Background technique [0002] The chemical synthesis of protein is an important scientific frontier field in the world today, and many countries have invested a lot of human, material and financial resources in this field. However, there is still relatively little work in the field of protein chemical synthesis in my country. This research will start with the method of protein synthesis and carry out related research. [0003] The solid-phase peptide synthesis technology based on Fmoc protection is currently a widely used method for synthesizing peptides. When the peptide synthesizer appeared, the efficiency of peptide synthesis was greatly improved. However, the solid-phase peptide synthesis technology has many defects that restrict its application, such as the by-product aspartimide when the Fmoc protecting group is removed under alkaline ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/22C07C323/59C07K7/06
CPCY02P20/55C07C319/22C07C269/06C07C271/22C07C323/59C07C381/04C07K7/06
Inventor 董甦伟李景威李耀豪
Owner PEKING UNIV
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