Peracylated proteins and synthetic polypeptides and process for making the same

• US 5,986,050 A
• Filed: 12/22/1997
• Issued: 11/16/1999
• Est. Priority Date: 12/26/1996
• Status: Expired due to Term

• Current Assignee: Poly-Med, Inc.
• Original Assignee: Poly-Med, Inc.
• Inventors: Shalaby, Shalaby W., Corbett, Joel T., Allan, Jacqueline M.
• Primary Examiner(s): Tsang, Cecilia
• Assistant Examiner(s): Mohamed, Abdel A.
• Application Number:
  US08/996,366
• Time in Patent Office: 694 Days
• Field of Search: 530/345, 530/303, 530/342, 530/356, 530/378, 530/402
• US Class Current: 530/345
• CPC Class Codes: C07K 1/113 without change of the primary structure
• CPC Class Codes: C07K 14/415 from plants
• CPC Class Codes: Y10T 428/29 Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
• CPC Class Codes: Y10T 428/2913 Rod, strand, filament or fiber
• CPC Class Codes: Y10T 428/2915 including textile, cloth or fabric

Abstract

A method for modifying a protein or polypeptide is disclosed which includes the steps of dispersing a protein or polypeptide in an essentially non-aqueous medium and peracylating the protein or polypeptide with a cyclic anhydride having a carbon chain substituent selected from the group consisting of alkyl and alkenyl groups. Most preferably, the cyclic anhydride is succinic anhydride, although glutaric anhydride may also be employed. Preferably, the step of peracylating the protein or polypeptide is performed in the presence of an acid catalyst, most preferably ρ-toluene sulfonic acid. The resultant modified protein or polypeptide may be employed in numerous applications including drug delivery, absorbable sutures, and thermoplastic films and molded articles.

Claims

1. A melt-processable soy protein composition made by the process comprising the steps of:

dispersing a soy protein in an essentially non-aqueous medium; and

peracylating the soy protein with at least two acyl groups per protein chain by reacting the protein with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

2. The soy protein composition set forth in claim 1 wherein said essentially non-aqueous medium comprises acetic acid.

3. The soy protein composition set forth in claim 1 wherein said essentially non-aqueous medium comprises propionic acid.

4. The protein composition set forth in claim 1 wherein said acid catalyst comprises ρ

-toluene sulfonic acid.

5. A melt-processable, synthetic polypeptide composition made by the process comprising the steps of:

dispersing a synthetic polypeptide in an essentially non-aqueous medium; and

peracylating the synthetic polypeptide with at least two acyl groups per synthetic polypeptide chain by reacting the synthetic polypeptide with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

6. The synthetic polypeptide composition set forth in claim 5 wherein said essentially non-aqueous medium comprises acetic acid.

7. The synthetic polypeptide composition set forth in claim 5 wherein said essentially non-aqueous medium comprises propionic acid.

8. A method for modifying a soy protein or synthetic polypeptide comprising the steps of:

dispersing a soy protein or synthetic polypeptide in an essentially non-aqueous medium; and

peracylating the soy protein or synthetic polypeptide with at least two acyl groups per soy protein or synthetic polypeptide chain by reacting the soy protein or synthetic polypeptide with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

9. The method set forth in claim 8 wherein said cyclic anhydride comprises succinic anhydride.

10. The method set forth in claim 8 wherein said cyclic anhydride comprises glutaric anhydride.

11. The method set forth in claim 8 wherein said acid catalyst comprises ρ

-toluene sulfonic acid.

12. A modified, soy protein-based article made by the process comprising the steps of:

forming a soy protein into an article;

subjecting the article to an essentially non-aqueous medium;

surface peracylating the article with a cyclic anhydride having a carbon chain substituent comprising at least eight carbon atoms per chain and selected from the group consisting of alkyl and alkenyl groups in the presence of an acid catalyst.

13. The modified, soy protein-based article set forth in claim 12 wherein said article comprises a suture.

14. The modified, soy protein-based article set forth in claim 12 wherein said article comprises a fabric.

15. The modified, soy protein-based article set forth in claim 12 wherein said cyclic anhydride comprises succinic anhydride.

16. The modified, soy protein-based article set forth in claim 12 wherein said cyclic anhydride comprises glutaric anhydride.