# US 9,752,137 B2 · Compounds, compositions and methods for the preparation of peptide/protein conjugates

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- Number: US 9,752,137 B2
- Document ID: US9752137B2
- Status: Granted
- Kind: B2
- Application number: 14/727,163
- Filed: 2015-06-01
- Published: 2016-11-17
- Granted: 2017-09-05
- Earliest claimed: 2015-05-11
- Assignees: The University of Hong Kong Shenzhen Institute of Research and Innovation
- Applicants: The University of Hong Kong Shenzhen Institute of Research and Innovation
- Inventors: Xuechen Li; Chun Ling Tung; Clarence Tsun Ting Wong
- Web page: https://patentgrep.com/patent/US9752137B2

## CPC

- C12N 9/82: Asparaginase {(3.5.1.1)}
- C07K 7/06: having 5 to 11 amino acids
- C07K 14/765: Serum albumin, e.g. HSA
- C12Y 305/01001: Asparaginase (3.5.1.1)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- C12Y: ENZYMES

## Abstract

Compounds, compositions and methods for the preparation of peptide/protein conjugates, said method comprising a step of reacting a compound (2) represented by the formula (2) with a compound (3) represented by the formula (3) to obtain compound (1) represented by the formula (1), wherein R′ represents substituent, and R represents H or at least one substituents. Also disclosed is a kit comprising the compound.

## Claims

### Claim 1

A compound represented by formula (1),
Wherein R′ represents an amino acid residue, a peptide residue and/or a protein residue, and R represents H or at least one substituent.

### Claim 2 (depends on 1)

The compound of claim 1, wherein said peptide residue is a synthetic or natural peptide residue.

### Claim 3 (depends on 1)

The compound of claim 1, wherein said protein residue is a native protein residue or recombinant protein residue.

### Claim 4 (depends on 1)

The compound of claim 1, wherein said protein residue is an enzyme residue or antibody residue.

### Claim 5 (depends on 1)

The compound of claim 1, wherein said peptide residue comprises at least one lysine residue in the sequence.

### Claim 6 (depends on 1)

The compound of claim 1, wherein said R is selected from alkyl, epoxide, amide, amine, ketone, aldehyde, phosphate, sulfate, halide, nitrile, nitro, azo, thiol, carboxylic acid, alkyne, ester, ether, alkene, or hydroxyl group.

### Claim 7 (depends on 1)

The compound of claim 1, wherein said compound is obtained by reacting a compound represented by formula (2) with a compound represented by formula (3),
R′—NH2 (2)
Wherein R′ represents an amino acid residue, a peptide residue and/or a protein residue, and R represents H or at least one substituent, said compound represented by formula (3) is selected from compounds 1 to 14:

### Claim 8 (depends on 1)

The compound of claim 1, wherein said R is linked with a poly(ethylene glycol) (PEG), a peptide, a drug, a carbohydrate, a fluorescent probe, DNA/RNA, a lipid, or combinations thereof.

### Claim 9

A composition comprising a compound represented by the formula (1),
Wherein R′ represents an amino acid residue, a peptide residue and/or a protein residue, and R represents H or at least one substituent.

### Claim 10

A kit comprising: (i) a compound represented by the formula (1),
Wherein R′ represents an amino acid residue, a peptide residue and/or a protein residue, and R represents H or at least one substituent; and (ii) a solvent.