Native ligation process

Patent metadata

Field	Value
Publication number	US-9796758-B2
Application number	US-201314386490-A
Country	US
Kind code	B2
Filing date	Mar 18, 2013
Priority date	Mar 21, 2012
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

A method for producing a polypeptide, includes at least one native ligation step using a peptide functionalized with a selenium group. The selenium peptides and compounds are also described.

First claim

The invention claimed is:

1. A functionalized peptide selected from:
a) the peptide of formula (I): X 1 —N(CH 2 CH 2 SeH) 2 ; or
b) the peptide of formula (I′):

in which X 1 represents a peptide fragment and the —N(CH 2 CH 2 SeH) 2 group or

group forms an amide bond with the C═O termination of the amino acid residue of the peptide fragment X 1 which is in the C-terminal position.

2. The functionalized peptide according to claim 1 , in which X 1 comprises from 2 to 300 amino acid residues.

3. A compound selected from:
a) the compound of formula (III′):

b) the compound of formula (III″):

4. A functionalized polymer resin, with the structure (V):

Or the structure (V′):

in which, □ represents a solid support, Trt represents a triphenylmethyl group optionally substituted by one or more substituents, X 1 represents a peptide fragment.

5. A polymer resin comprising a peptide fragment corresponding to formula (VII) or (VII′):

in which, □ represents a solid support, Trt represents a triphenylmethyl group optionally substituted by one or more substituents, X 1 represents a peptide fragment.

6. The polymer resin according to claim 4 , in which the solid support □ is selected from the group consisting of a polystyrene, a polyacrylamide, a polyethylene glycol, a cellulose, a polyethylene, a polyester, a latex, a polyamide, a polydimethylacrylamide, a polyethylene glycol-polystyrene copolymer, a polyethylene glycol-polyacrylamide copolymer and derivatives thereof.

7. The polymer resin according to claim 5 , in which the solid support □ is selected from the group consisting of a polystyrene, a polyacrylamide, a polyethylene glycol, a cellulose, a polyethylene, a polyester, a latex, a polyamide, a polydimethylacrylamide, a polyethylene glycol-polystyrene copolymer, a polyethylene glycol-polyacrylamide copolymer and derivatives thereof.

8. A polypeptide synthesis kit comprising at least one compound according to claim 3 .

9. The functionalized peptide according to claim 2 , in which X 1 comprises from 5 to 100 amino acid residues.

10. The functionalized peptide according to claim 2 , in which X 1 comprises from 8 to 50 amino acid residues.

11. The functionalized peptide according to claim 4 , wherein the triphenylmethyl group is substituted by one or more substituents selected from group consisting of chlorine, methoxy, methyl, fluorine and cyano.

12. The functionalized peptide according to claim 5 , wherein the triphenylmethyl group is substituted by one or more substituents selected from group consisting of chlorine, methoxy, methyl, fluorine and cyano.

Assignees

• Centre Nat De La Rech Scient (Cnrs)
• Pasteur Institut
• Univ Lille Ii Droit & Sante
• Centre Nat Rech Scient

Inventors

• Melnyk Oleg
• Raibaut Laurent
• Ollivier Nathalie

Classifications

• C08G65/48

  Polymers modified by chemical after-treatment · CPC title

• C07K1/026 Primary

  by fragment condensation in solution · CPC title

• C08F10/02

  Ethene · CPC title

• C07K1/042

  characterised by the nature of the carrier · CPC title

• C07D293/02

  not condensed with other rings · CPC title