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Arylation or alkynylation modification method of natural amino acid-oriented polypeptide C (sp3)-H bond

A natural amino acid and modification method technology, applied in the field of post-synthesis modification of polypeptides, can solve the problems of lack of structural diversity, poor pharmacological properties, etc., and achieve a wide range of substrate applicability, high atom economy and step economy, and reaction selection sex high effect

Pending Publication Date: 2021-08-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, natural peptides are often characterized by poor pharmacological properties and lack of structural diversity

Method used

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  • Arylation or alkynylation modification method of natural amino acid-oriented polypeptide C (sp3)-H bond
  • Arylation or alkynylation modification method of natural amino acid-oriented polypeptide C (sp3)-H bond
  • Arylation or alkynylation modification method of natural amino acid-oriented polypeptide C (sp3)-H bond

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Add dipeptide Phth-L-Ala-Asp(OH)-OMe (696.6mg, 2.0mmol), 4-iodophenol (880.2mg, 4.0mmol), catalyst 4 into a clean and dry 10mL Shrek tube (Triphenylphosphine) palladium (231.1mg, 10mol%), oxidant silver trifluoroacetate (342.1mg, 3.0mmol), additive potassium dihydrogen phosphate (544.4mg, 4.0mmol) and toluene (4.0mL), 20 ℃ air React in the atmosphere for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, then diluted with 10 mL of ethyl acetate, concentrated under reduced pressure to remove the solvent, and purified by silica gel column chromatography (the elution solvent was CH 2 Cl 2 :MeOH:AcOH=100:2:1, volume ratio) to obtain 768.1 mg of a white solid product (ie product 1), with a yield of 87.2%.

[0040] Data characterization of dipeptide raw material Phth-L-Ala-Asp(OH)-OMe:

[0041]

[0042] M.p.=133-135℃.

[0043] 1 H NMR (400MHz, CDCl 3 )δ9.80(br,1H),7.87-7.83(m,2H),7.75-7.71(m,2H),7.07(d,J=8.0Hz,1H),4.95...

Embodiment 2

[0054] Example 2: The experimental process of Example 2 was repeated in Example 1, except that the "reaction time was adjusted to 24 hours", and finally 791.0 mg of white solid product was obtained, with a yield of 89.8%.

Embodiment 3

[0055] Example 3: The experimental process of Example 3 was repeated in Example 1, the only difference being that "reaction time was adjusted to 48 hours", and finally 791.9 mg of white solid product was obtained, with a yield of 89.9%.

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Abstract

The invention discloses an arylation or alkynylation modification method of a natural amino acid-oriented polypeptide C (sp3)-H bond. The method comprises the following steps of: in the presence of an oxidant, a catalyst, an additive and a solvent, by taking a compound shown in a formula (III) or a formula (IV) as a modification raw material, respectively performing arylation or alkynylation modification of the C (sp3)-H bond on an alanine side chain in a compound shown in a formula (I) or a formula (II). According to the method disclosed by the invention, a series of fluorescence-labeled alanine-containing polypeptide derivatives, side-chain-modified tyrosine-containing polypeptide derivatives, side-chain-modified phenylalanine-containing polypeptide derivatives and alkynyl-modified alanine-containing polypeptide derivatives can be synthesized. The method disclosed by the invention has the advantages that a guide group does not need to be introduced in advance or subsequently removed, the atom economy and gait economy are high, the conditions are mild, the substrate applicability range is wide, the method is not influenced by amino acid configuration, and the like, and is a polypeptide modification method with excellent popularization prospects.

Description

technical field [0001] The invention belongs to the field of post-synthetic modification of polypeptides, and relates to a natural amino acid-oriented polypeptide C(sp 3 )-H bond arylation or alkynylation modification method. Background technique [0002] Polypeptides generally refer to compounds with less than 100 amino acids connected by peptide bonds, with a relative molecular mass of less than 10,000, and play an important role in physiological activities such as cell proliferation and differentiation, body immunity, and tumor lesions. Peptides have also attracted considerable attention as a therapeutic approach in terms of their ability to regulate various cellular functions in organisms, highly specific binding to receptors, and targeting to protein surfaces. However, natural peptides are often characterized by poor pharmacological properties and lack of structural diversity. Post functionalization of peptides can significantly improve their physical and chemical pro...

Claims

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Application Information

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IPC IPC(8): C07K1/107
CPCC07K1/113
Inventor 翁意意蔡梦薇陈卓朱美洁
Owner ZHEJIANG UNIV OF TECH
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