Arylation or alkynylation modification method of natural amino acid-oriented polypeptide C (sp3)-H bond
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF2 Cites 4 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
However, natural peptides are often characterized by poor
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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%.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more