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Method for producing d-form or l-form amino acid derivative having thiol group

A manufacturing method, amino acid technology, applied in the preparation of organic compounds, biochemical equipment and methods, preparation of thiols, etc., can solve the problems such as not specifically mentioned manufacturing, not reaching the level of manufacturing, etc.

Active Publication Date: 2016-03-09
GLYTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, among these, there is no particular mention of the production of amino acids having desired substituents such as thiol groups in their side chains, etc.
In addition, the enzyme is substrate-specific, so the enzyme cannot be said to be effective for amino acid derivatives with bulky substituents such as a protected thiol group in the beta position
Subsequent production of polymeric D- or L-proteins, the optically active β-thioamino acid derivatives that can be used as the binding site of NCL, so far, have not yet achieved the industrial production of D- or L-proteins The extent to which the implementation of the manufacturing

Method used

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  • Method for producing d-form or l-form amino acid derivative having thiol group
  • Method for producing d-form or l-form amino acid derivative having thiol group
  • Method for producing d-form or l-form amino acid derivative having thiol group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0127] As the protecting group for the amino group, those generally used for the protecting group of the amino group can be used, for example, a fat-soluble protecting group described later can be used. In one embodiment of the present invention, for example, 9-fluorenylmethoxycarbonyl (Fmoc) or tertiary butoxycarbonyl (Boc), allyloxycarbonate (Alloc) and other carbonate-containing group, acyl group such as acetyl group (Ac), protective group such as aryl group, benzyl group, etc. To introduce a protecting group, for example, to introduce a Boc group, add Boc to the reaction system 2 O THF solution method and so on. The introduction of the protecting group of the amino group can be carried out by a known method other than the above-mentioned method depending on the protecting group. In addition, the deprotection of the protecting group of the amino group can be carried out by treating with an acid or a base. For example, when the protecting group is a Boc group, an acid suc...

Embodiment

[0219] Synthesis of Optically Active Aromatic Amino Acid Derivatives with a Thiol Group at the β Position Using Aromatic Amino Acids as Starting Materials

[0220] As shown in the following reaction formula, a synthesis reaction of D,L-phenylalanine having a thiol group at the β-position is carried out using an aromatic amino acid as a starting material. The compound numbers described after the compound names in the synthesis examples represent the compound numbers described in the following reaction formulas.

[0221]

Synthetic example 1

[0222] (Synthesis Example 1) D,L-Phenylalanine Methyl Ester Hydrochloride (Compound 6)

[0223] Under argon, D,L-phenylalanine (10.0 g, 60.5 mmol) was added to methanol (48.4 mL), and after the solution was cooled to 0° C., sulfinyl chloride (4.8 ml, 66.6 mmol) was added dropwise. Afterwards, it was stirred at reflux for 1 hour. After the reaction solution was concentrated under reduced pressure, recrystallization was performed using a mixed solvent of 5 ml of methanol and 80 mL of diethyl ether to obtain D,L-phenylalanine methyl ester hydrochloride (compound 6) (11.8 g).

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Abstract

The present invention addresses the problem of providing a simple method for producing, at a high yield, an optically active D-form and / or L-form amino acid derivative having a thiol group in a side chain. Provided are: a method for producing an amino acid derivative having a thiol group in a side chain, said method being characterised by producing an intermediate composition that includes D-forms and L-forms of an amino acid derivative which has a thiol group at the beta-position, causing a D- or L-amino acid selective hydrolase to react, and separating the hydrolysed D- or L-amino acid derivatives; and an intermediate therefor.

Description

technical field [0001] The present invention relates to a method for producing D-type or L-body amino acid derivatives with thiol groups in their side chains. Furthermore, the present invention relates to an intermediate used in a method for producing a D-form or L-form amino acid derivative having a thiol group in its side chain. Background technique [0002] In recent years, with the progress of research and development of biomedicine, examples of analyzing the structure and function of synthetic peptides and proteins, and examples of using peptides and proteins as medicines are increasing. Peptides and proteins are composed of amino acids. Except for the side chain substituents of the α-amino acids that make up proteins are hydrogen atoms, the α carbon atoms are asymmetric atoms, so there are mirror images called D-form and L-body. things exist. Peptides and proteins that exist in vivo are composed of L-amino acids. Therefore, to synthesize peptides and proteins that ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00C07C319/28C07C323/58C07C323/59C07B57/00C12N9/80
CPCC07B57/00C12N9/80C07B2200/07C12P41/001C07C319/28Y02P20/55C07C323/58C07C323/59C12Y305/01014C07C319/02C12P13/222C12P13/225
Inventor 梶原康宏森下靖仁村濑健文
Owner GLYTECH
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