Protein and/or peptide modification molecule

Patent metadata

Field	Value
Publication number	US-2022204481-A1
Application number	US-202017432838-A
Country	US
Kind code	A1
Filing date	Feb 28, 2020
Priority date	Feb 28, 2019
Publication date	Jun 30, 2022
Grant date	—

Abstract

An object of the present invention is to provide a technique that allows other molecules/substances to be more selectively linked to the N-terminus in a simple and efficient manner, even in natural proteins etc. This object is achieved by reacting a compound represented by formula (1) or a salt thereof, or a hydrate or solvate of the compound or a salt thereof with a protein and/or peptide.

First claim

In the claims:

1 . A reagent for protein and/or peptide modification, comprising a compound represented by formula (1) or a salt thereof, or a hydrate or solvate of the compound or a salt thereof,

wherein one of R 1 and R 2 represents —N(—R 4 )— (wherein R 4 represents an organic group or a group derived from an inorganic material), and the other represents ═N—; and R 3 represents a hydrogen atom, an organic group, or a group derived from an inorganic material.

2 . The reagent according to claim 1 , wherein the compound is represented by formula (1A):

wherein R 4 is as defined above.

3 . The reagent according to claim 1 , wherein the organic group is a group derived from an organic molecule or an organic molecular complex, and the organic molecule or the organic molecular complex is a functional substance.

4 . The reagent according to claim 3 , wherein the functional substance is a pharmaceutical compound, a luminescent molecule, a macromolecular compound, a ligand, a molecule to which a ligand binds, an antigenic protein, an antibody, a protein, a nucleic acid, a saccharide, a lipid, a cell, a virus, a label, a carbon electrode, a carbon nanomaterial, a linker, a spacer molecule, or a complex or linked molecule thereof.

5 . The reagent according to claim 1 , wherein the inorganic material is an electrode material, metal fine particles, metal oxide fine particles, semiconductor particles, or magnetic particles.

6 - 8 . (canceled)

9 . A method for producing a compound represented by formula (1) or a salt thereof, or a hydrate or solvate of the compound or a salt thereof,

wherein one of R 1 and R 2 represents —N(—R 4 )— (wherein R 4 represents an organic group or a group derived from an inorganic material), and the other represents ═N—; and R 3 represents a hydrogen atom, an organic group, or a group derived from an inorganic material,
the method comprising:
reacting a compound represented by formula (5):
R 4 -R 9 (5),

wherein R 4 represents an organic group or a group derived from an inorganic material; and R 9 represents —NR 9a R 9b (wherein R 9a and R 9b are the same or different and each represents a hydrogen atom or an alkyl group),
with a compound represented by formula (6):

wherein R 10 represents an electron-withdrawing group; R 11 represent —R 11a —R 12 (wherein R 11a represents a single bond or a linker; and R 12 represents a carrier); n represents 0 or 1; and m represents an integer of 1 to 5.

10 . A compound represented by formula (6′):

wherein R 10 represents an electron-withdrawing group; R 11a represents a single bond or a linker; R 12 represents a carrier; and m represents an integer of 1 to 5.

11 . A compound represented by formula (7) or a salt thereof, or a hydrate or solvate of the compound or a salt thereof,

wherein one of R 1 and R 2 represents —N(—R 4 )— (wherein R 4 represents an organic group or a group derived from an inorganic material), and the other represents ═N—; R 3 represents a hydrogen atom, an organic group, or a group derived from an inorganic material; a double line composed of a dotted line and a solid line represents a single bond or a double bond; R 13 represents a group in which the N-terminal amino acid residue and —NH— adjacent thereto are excluded from a protein or peptide; and R 14 represents the side chain of the N-terminal amino acid residue of the protein or peptide.

12 . A method for producing the compound or a salt thereof, or a hydrate or solvate of the compound or a salt thereof according to claim 11 , the method comprising reacting a protein and/or a peptide with a compound represented by formula (1) or a salt thereof, or a hydrate or solvate of the compound or a salt thereof,

wherein one of R 1 and R 2 represents —N(—R 4 )— (wherein R 4 represents an organic group or a group derived from an inorganic material), and the other represents ═N—; and
R 3 represents a hydrogen atom, an organic group, or a group derived from an inorganic material.

Assignees

• Univ Osaka

Inventors

• Hayashi Takashi
• Onoda Akira
• Inoue Nozomu

Classifications

• C07K17/08

  the carrier being a synthetic polymer · CPC title

• G01N33/532

  Production of labelled immunochemicals · CPC title

• C07D249/04

  1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles · CPC title

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title