# US 8,772,450 B2 · Beta-amino acids

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- Number: US 8,772,450 B2
- Document ID: US8772450B2
- Status: Granted
- Kind: B2
- Application number: 13/463,212
- Filed: 2012-05-03
- Published: 2013-01-24
- Granted: 2014-07-08
- Earliest claimed: 1997-03-04
- Assignees: Wisconsin Alumni Research Foundation
- Applicants: Samuel H. Gellman; Daniel H. Appella; Hee-Seung Lee; Paul LePlae; Emilie Porter; Xifang Wang; Matthew Woll
- Inventors: Samuel H. Gellman; Daniel H. Appella; Hee-Seung Lee; Paul LePlae; Emilie Porter; Xifang Wang; Matthew Woll
- Web page: https://patentgrep.com/patent/US8772450B2

## CPC

- C07D 207/16: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07C 237/24: having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C07D 211/60: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 211/62: attached in position 4
- C07B 2200/11: Compounds covalently bound to a solid support
- C07C 2601/14: The ring being saturated
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Disclosed are β-amino acid monomers containing cylcoalkyl, cycloalkenyl, and heterocylic substituents which encompass the α and β carbons of the peptide backbone and β-polypeptides made from such monomers. Method of generating combinatorial libraries of polypeptides containing the β-peptide residues and libraries formed thereby are disclosed.

## Claims

### Claim 1

A composition comprising a polypeptide comprising the formula:
wherein Z is selected from the group consisting of:
and wherein each residue's X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted or unsubstituted C3-C8 cycloalkyl, cycloalkenyl or heterocyclic ring having one or more nitrogen atoms as the sole heteroatom, the substituents being selected from the group consisting of hydroxy, linear or branched C1-C6-alkyl, alkenyl, alkynyl; hydroxy-C1-C6-alkyl, amino-C1-C6-alkyl, C1-C6-alkyloxy, C1-C6-alkyloxy-C1-C6-alkyl, amino, mono- or di-C1-C6-alkylamino, carboxamido, carboxamido C1-C6-alkyl, sulfonamido, sulfonamido-C1-C6-alkyl, urea, cyano, fluoro, thio, C1-C6-alkylthio, mono- or bicyclic aryl, mono- or bicyclic heteraryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, and heteroaryl-C1-C6-alkyl;
or X and Y are independently selected from the group consisting of hydroxy, linear or branched C1-C6-alkyl, alkenyl, alkynyl; hydroxy-C1-C6-alkyl, amino-C1-C6-alkyloxy, C1-C6-alkyloxy-C1-C6-alkyl, amino, mono- or di-C1-C6-alkylamino, carboxamido, carboxamido-C1-C6-alkyl, sulfonamido, sulfonamido-C1-C6-alkyl, urea, cyano, fluoro, thio, C1-C6-alkylthio, mono- or bicyclic aryl, mono- or bicyclic heteraryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, and heteroaryl-C1-C6-alkyl; and
wherein m is 1, and
wherein n and p are 1.

### Claim 2

A composition comprising a polypeptide comprising the formula:
wherein Z is a single bond; and
each residue's X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted C4-C6 cycloalkyl, cycloalkenyl, or heterocyclic ring having one nitrogen atom as the sole hetero atom;
wherein m is 1, and
wherein n and p are 1.

### Claim 3 (depends on 2)

The composition of claim 2, wherein X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted cyclopentyl, cyclohexyl, pyrrolidinyl, or piperidinyl ring.

### Claim 4 (depends on 3)

The composition of claim 3, wherein the substituent is selected from the group consisting of amino, mono- or di-C1-C6-alkylamino, carboxamido, sulfonamido, urea, thio, and C1-C6-alkylthio.

### Claim 5 (depends on 2)

The composition of claim 2, wherein X and Y combined, together with the carbon atoms to which they are bonded, independently define an amino-substituted cyclopentyl, amino-substituted cyclohexyl, amino-substituted pyrrolidinyl, or amino-substituted piperidinyl ring.

### Claim 6

A composition comprising a polypeptide comprising the formula
wherein X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted C3-C8 cycloalkyl, cycloalkenyl or heterocyclic ring having one or more nitrogen atoms as the sole heteroatom, the substituents being selected from the group consisting of hydroxy, linear or branched C1-C6-alkyl, alkenyl, alkynyl; hydroxy-C1-C6-alkyl, amino-C1-C6-alkyl, C1-C6-alkyloxy, C1-C6-alkyloxy-C1-C6-alkyl, amino, mono- or di-C1-C6-alkylamino, carboxamido, carboxamido-C1-C6-alkyl, sulfonamido, sulfonamido-C1-C6-alkyl, urea, cyano, fluoro, thio, C1-C6-alkylthio, mono- or bicyclic aryl, mono- or bicyclic heteraryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, and heteroaryl-C1-C6-alkyl; and
n is a positive integer greater than 3.

### Claim 7 (depends on 6)

The composition of claim 6, wherein X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted C4-C6 cycloalkyl, cycloalkenyl, or heterocyclic ring having one nitrogen atom as the sole hetero atom.

### Claim 8 (depends on 6)

The composition of claim 6, X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted cyclopentyl, cyclohexyl, pyrrolidinyl, or piperidinyl ring.

### Claim 9 (depends on 6)

The composition of claim 6, wherein X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted cyclopentyl, cyclohexyl, pyrrolidinyl, or piperidinyl ring, wherein the substituent is selected from the group consisting of amino, mono- or di-C1-C6-alkylamino, carboxamido, sulfonamido, urea, thio, and C1-C6-alkylthio.