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Novel compound, production method therefor, and application therefor

A compound, selected technology, applied in the preparation method of peptides, chemical instruments and methods, organic chemistry, etc., can solve the problems that cannot be applied

Active Publication Date: 2016-05-18
TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the case of labeling low-molecular-weight compounds, these methods cannot be applied, and in order to remove residues of reagents with similar molecular weights, purification by more complicated chromatography, etc. is required

Method used

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  • Novel compound, production method therefor, and application therefor
  • Novel compound, production method therefor, and application therefor
  • Novel compound, production method therefor, and application therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0380] As an example of the compound of the present invention, the synthesis of compound A is shown below.

[0381] Synthesis of Compound A (6-chlorosulfenyl-5-nitronicotinic acid carboxamide resin)

[0382] Compound A was synthesized by the following route.

[0383] [chem 67]

[0384]

[0385] Resin: Cross-linked product of polyethylene glycol (MethylChemMatrix (registered trademark) resin)

[0386] (1) Synthesis of Compound 2

[0387] Compound 1 (25 g, 0.180 mol) was placed in a 500 ml eggplant-shaped bottle, and fuming nitric acid (1.52) (125 ml) was added. While stirring, it heated slowly using an oil bath, and stirred for 5 hours under the temperature condition of 50 degreeC. Heating was stopped, and after natural cooling to room temperature, the reaction solution was concentrated under reduced pressure. The obtained residue was cooled in an ice bath, recrystallized using methanol as a solvent, and the solid obtained by filtration was dried under reduced pressure ...

Embodiment 2

[0403] As an example of the compound of the present invention, the synthesis of Compound B is shown below.

[0404] Synthesis of Compound B (5-((6-(methylaminoresin)-6-oxohexyl)amino)-6-oxohexyl)carbonyl)-3-nitropyridine-2-sulfenyl chloride)

[0405] Compound B was synthesized by the following route.

[0406] [chem 68]

[0407]

[0408] Resin: Cross-linked product of polyethylene glycol (MethylChemMatrix (registered trademark) resin)

[0409] (1) Synthesis of Compound 8

[0410] 9-Fluorenylmethoxycarbonylaminocaproic acid (compound 7, 632.4 mg, 1.79 mmol), (O-(7-azabenzotriazol-1-yl)- N,N,N',N'-tetramethyluronium hexafluorophosphate) (540.6mg, 1.76mmol), DMF (16ml), diisopropylethylamine (257.0μl, 1.79mmol) for 1 min Shake to stir. Take 511.7 mg of aminomethyl-ChemMatrix resin (H in the formula) in an additionally prepared 60 ml polypropylene filter tube 2N-resin, functional group substitution rate 0.70mmol / g), to which was added the solution in the above 15ml tube at...

Embodiment 3

[0422] Modification of the octaarginine derivative of the compound captopril (compound 13) having an SH group using compound A was carried out through the following synthetic route.

[0423] [chem 69]

[0424]

[0425] Resin: Cross-linked product of polyethylene glycol (MethylChemMatrix (registered trademark) resin)

[0426] To a 10-ml glass test tube containing compound A and a stir bar, 90% formic acid aqueous solution (2 ml) was added under ice-cooling, followed by gentle stirring to replace the solvent. After removing the washing solution with a Pasteur pipette, 90% formic acid aqueous solution was added again, and the same washing was repeated five times. In an additionally prepared 30ml Erlenmeyer flask, the peptide Ac-Arg containing octa-arginine consisting of 10 residues was 8 -Acp-Cys(tBu)-NH 2 • TFA salt (143.37 mg) was dissolved in 90% formic acid (1 ml), and the resulting aqueous solution was added to the 10 ml glass test tube containing the above compound A ...

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Abstract

[Problem] To provide a heretofore completely different and novel peptide synthesis technique, and to provide a novel compound that enables the synthesis / creation of a novel artificial functional protein and the synthesis / creation of a novel functional peptide, as well as a production method for said compound. [Solution] A compound represented by formula (I) or a salt thereof.

Description

【Technical field】 [0001] The present invention relates to novel compounds, processes for their manufacture and uses thereof. More specifically, the present invention provides a compound having a sulfenylpyridine structure supported on a polymer carrier, a method for producing the compound, a novel peptide synthesis method using the compound, and the like. 【Background technique】 [0002] Conventionally, in the analysis and detection of biomolecules such as proteins, peptides, and nucleic acids, techniques for producing labeled substances using labeling substances that bind to the biomolecules have been widely used in the fields of biology and molecular biology. A specific example of molecular labeling is biotin labeling. In order to improve the sensitivity of various detection systems or purification of physiologically active substances, a system utilizing the strong affinity of avidin and biotin has been developed. Furthermore, a biotin-labeled substance is required in thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/337C07K1/04C07K1/08C07K2/00C07K5/06C07K5/08C07K5/10C07K7/06C07K17/02C07D213/82
CPCC07D207/16C07D213/82C07K1/042C07K1/067C07K5/1013C07K7/16C08G65/329C08G65/337C08L2203/02C07K7/06C07K7/08
Inventor 林良雄梶山晶大田口晃弘福元谦太郎
Owner TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES
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