A method for synthesizing amino acid n-methylation and its product and application

A methylation and amino acid technology, applied in the preparation of cyanide reaction, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of poor industrialization prospects, many reaction steps, and highly toxic reagents, and achieve structural pertinence. Strong, low cost, simple operation effect
CN105949078BActive Publication Date: 2018-09-21SOUTH CHINA AGRI UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
SOUTH CHINA AGRI UNIV
Publication Date
2018-09-21

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Abstract

The invention relates to the technical field of amino acid polypeptide synthesis, and discloses an amino acid N-methylation synthesis method, and a product and an application thereof. According to the invention, through benzyl protection upon the carboxyl group of amino acid and through trifluoroacetyl protection upon the amino group, N-methylated amino acid can be obtained after methylation. The N-methyl(trifluoroacetyl)-amino acid benzyl ester prepared by the method provided by the invention can be directly used in polypeptide synthesis, such that an amino acid benzyl ester product with an N-methyl structure can be obtained. Also, the compound has good deprotection selectivity, and selective deprotection can be carried out upon the N-terminal and the C-terminal. Compared to a Ag2O / CH3I / Boc method (high toxicity and high cost) and a NaH / (CH3O)2SO2 method (high toxicity) abroad, the method provided by the invention has high yield. With the use of nontoxic reagents, the method is safe and nontoxic, and has the advantages of simple operation, common and easy-to-obtain raw material reagents, low cost, and high structural selectivity. The obtained product has low racemization possibility. The method has a good industrial prospect.
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Description

technical field

[0001] The invention belongs to the technical field of amino acid polypeptide synthesis, and in particular relates to a method for synthesizing amino acid N-methylation and its product and application. Background technique

[0002] N-methyl-amino acid is an important fragment of most biologically active peptide natural products, which are reflected in cyclic peptides such as Destruxin, Hirsutellide and chain peptides such as tasiamide. These compounds play an important role in the backbone structure and activity of the polypeptide. The introduction of the methyl group to the polypeptide composed of amino acids after N-methylation sterically affects the structural form of the polypeptide skeleton, reducing the possibility of isomer formation; electronically weakens the electron-absorbing effect of the amide bond N on the carbonyl carbon ability, increases the hydrolytic stability of the protein, and at the same time enhances the membrane permeability (lipophi...

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
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