Method for photocleavage of amide bonds

Patent metadata

Field	Value
Publication number	US-11845708-B2
Application number	US-202117486807-A
Country	US
Kind code	B2
Filing date	Sep 27, 2021
Priority date	Mar 12, 2021
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

The present disclosure provides a method for photocleavage of an amide bond, the method has mild reaction conditions and can realize the cleavage of amide bonds by using light. The method comprises the following steps: subjecting 2,4-dinitrofluorobenzene to a reaction with an amino group of a substance represented by structural formula I with an α-amino acid at the end to produce a compound 1 represented by structural formula II; then under light irradiation, subjecting the compound 1 to a cleavage reaction of amide bond;Wherein, R1 is the side chain group of α-amino acid; R2 is: aryl, aliphatic hydrocarbon, —CH(R)—COOH or polypeptide.

First claim

What is claimed is:

1. A method for photocleavage of an amide bond, comprising the steps of
subjecting 2,4-dinitrofluorobenzene to a reaction with an amino group of a substance represented by structural formula I with an α-amino acid at an end to produce a compound 1 represented by structural formula II;
under light irradiation, subjecting the compound 1 to a cleavage reaction of the amide bond according to reaction equation 1:

wherein R 1 is a side chain group of α-amino acid; R 2 aryl, aliphatic hydrocarbon group, or polypeptide group.

2. The method according to claim 1 , further comprising the following steps: dissolving 2,4-dinitrofluorobenzene in an organic solvent to obtain a first solution, then dissolving the substance represented by structural formula I with an α-amino acid at the end and NaHCO 3 in water to obtain a second solution, mixing the first solution and the second solution in a reaction vessel, and stirring and refluxing a resulting mixture at 40-100° C. under darkness for 3-10 h.

3. The method according to claim 1 , wherein a wavelength range for the light irradiation is 250-550 nm.

4. The method according to claim 1 , wherein a light irradiation time is 0.1 second to 6 h.

5. The method according to claim 2 , wherein the organic solvent is capable of dissolving the compound 1.

6. The method according to claim 5 , wherein the organic solvent is one or a combination of dimethyl sulfoxide, alcohol, ketone, nitrile, ether, and amide.

7. The method according to claim 6 , wherein the alcohol is methanol, ethanol, butanol, ethylene glycol, n-octanol or isopropanol; the ketone is acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; the nitrile is acetonitrile, propionitrile, isobutyronitrile, butyronitrile, malononitrile, benzonitrile, benzyl cyanide, succinonitrile or glutaronitrile; the ether is diethyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether, 2-methyltetrahydrofuran or diphenyl ether; and the amide is N,N-dimethylformamide or N,N-dimethylacetamide.

Assignees

• Nanjing University Of Technology

Inventors

• Chen Xiaoqiang
• Wei Tingwen
• Wang Jing
• Wang Yanyan

Classifications

• C07C227/04 Primary

  Formation of amino groups in compounds containing carboxyl groups · CPC title

• C07D209/20 Primary

  substituted additionally by nitrogen atoms, e.g. tryptophane · CPC title

• C07D235/22

  with hetero atoms directly attached to ring nitrogen atoms (C07D235/10 takes precedence) · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07C231/12 Primary

  by reactions not involving the formation of carboxamide groups · CPC title