# US 5,710,245 A · Alpha-helix mimetics and methods relating thereto

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- Number: US 5,710,245 A
- Document ID: US5710245A
- Status: Granted
- Kind: A
- Application number: 08/453,006
- Filed: 1995-05-30
- Granted: 1998-01-20
- Earliest claimed: 1993-06-18
- Assignees: Molecumetics, Ltd.
- Inventors: Michael Kahn
- Web page: https://patentgrep.com/patent/US5710245A

## CPC

- C07K 5/06139: {with the first amino acid being heterocyclic}
- C07K 1/1075: {by covalent attachment of amino acids or peptide residues}
- C07K 14/57545: {Neuropeptide Y}
- 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)

## Abstract

There are disclosed alpha-helix mimetics and methods relating to the same for imparting or stabilizing alpha-helicity to a peptide or protein. In one aspect, the alpha-helix mimetics contain six- or seven-membered rings covalently attached at the end or within the length of the peptide or protein. The alpha-helix mimetics render the resulting peptide or protein more stable with regard to thermal stability, as well as making the peptide or protein more resistant to proteolytic degredation. In addition, the alpha-helix mimetics may be used in standard peptide synthesis protocols.

## Claims

### Claim 1

An alpha-helix mimetic having the structure: ##STR19## wherein Z is an optional methylene moiety; R.sup.1 through R.sup.5 are each selected from naturally occurring amino acid side chain moieties independently selected from the group consisting of amino acids, alpha-helix mimetics and terminating moieties.

### Claim 2 (depends on 1)

The alpha-helix mimetic of claim 1 having the structure: ##STR20##

### Claim 3 (depends on 1)

The alpha-helix mimetic of claim 1 having the structure: ##STR21##

### Claim 4 (depends on 1)

The alpha-helix mimetic of claim 1 wherein the amino acid side chain moieties are selected from the amino acid side chains of glycine, alanine, valine, leucine, isoleucine, lysine, arginine, histidine, aspartic acid, glutamic acid, asparagine, glutamine, phenylalanine, tyrosine, tryptophan, cysteine, methionine, serine and threonine.

### Claim 5

An alpha-helix mimetic having the structure: ##STR22## wherein R.sup.1 through R.sup.4 are each selected from naturally occurring amino acid side chain moieties; and X and Y are independently selected from the group consisting of amino acids, alpha-helix mimetics and terminating moieties.

### Claim 6 (depends on 5)

The alpha-helix mimetic of claim 5 wherein the amino acid side chain moieties are selected from the amino acid side chains of glycine, alanine, valine, leucine, isoleucine, lysine, arginine, histidine, aspartic acid, glutamic acid, asparagine, glutamine, phenylalanine, tyrosine, tryptophan, cysteine, methionine, serine and threonine.

### Claim 7

An alpha-helix modified peptide or protein, comprising a peptide or protein and an alpha-helix mimetic, the alpha-helix mimetic being covalently attached to at least one amino acid of the peptide or protein, wherein the alpha-helix mimetic has the structure: ##STR23## wherein Z is an optional methylene moiety; R.sup.1 through R.sup.5 are each selected from naturally occurring amino acid side chain moieties; and at least X or Y is an amino acid of the peptide or protein.

### Claim 8 (depends on 7)

The alpha-helix modified peptide or protein of claim 7 wherein both X and Y are amino acids of the peptide or protein.

### Claim 9

An alpha-helix modified peptide or protein, comprising a peptide or protein and an alpha-helix mimetic, the alpha-helix mimetic being covalently attached to at least one amino acid of the peptide or protein, wherein the alpha-helix mimetic has the structure: ##STR24## wherein R.sup.1 through R.sup.4 are each selected from naturally occurring amino acid side chain moieties; and at least X or Y is an amino acid of the peptide or protein.

### Claim 10 (depends on 9)

The alpha-helix modified peptide or protein of claim 9 wherein both X and Y are amino acids of the peptide or protein.