Photoreactive benzoylphenylalanines and related peptides

• US 4,762,881 A
• Filed: 01/09/1987
• Issued: 08/09/1988
• Est. Priority Date: 01/09/1987
• Status: Expired due to Fees

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Kauer, James C.
• Primary Examiner(s): NOT, DEFINED
• Application Number:
  US07/001,874
• Time in Patent Office: 578 Days
• Field of Search: 525/54.11, 562/441, 530/334
• US Class Current: 525/54.11
• CPC Class Codes: C07C 2603/18 Fluorenes; Hydrogenated fluorenes
• CPC Class Codes: C07K 17/02 Peptides being immobilised on, or in, an organic carrier
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Provided is a benzoylphenylalanine of the formula: ##STR1## wherein ##STR2## is in the m or p position; and Pr is a protecting group which is easily cleavable in the presence of a peptide bond by a mild acid or base.

This benzoylphenylalanine group is incorporated into a peptide chain which can be attached to a solid substrate having a reactive hydrogen by exposure to low energy ultraviolet light.

Claims

1. A benzoylphenylalanine having the formula:

##STR18## wherein ##STR19## is in the m or p position; and

Pr is a protecting group which is easily cleavable in the presence of a peptide bond by a mild acid or base.

2. A benzoylphenylalanine of claim 1 wherein Pr is a bulky protecting group removable by acidic or by basic treatment.

3. A benzoylphenylalanine of claim 2 wherein Pr is OR where R is a branched chain alkyl of 3 to 10 carbon atoms or aralkyl or 7 to 15 carbon atoms.

4. A benzoylphenylalanine of claim 3 wherein ##STR20## is in the p position and R is a branched chain alkyl group of 4 to 10 carbon atoms.

5. A benzoylphenylalanine of claim 4 wherein R is t-butyl.

6. A benzoylphenylalanine of claim 3 wherein R is benzyl.

7. A benzoylphenylalanine of claim 3 wherein R is fluorenylmethyl.

10. A process for preparing a photoreactive polypeptide of claim 8 comprising:

(a) contacting a peptide chain of preselected length with a benzoylphenylalanine having the formula;

##STR24## where Pr is defined in claim 1;

(b) optionally removing the protecting group; and

(c) continuing the peptide chain to a preselected polypeptide sequence.

11. A process of claim 10 wherein Pr is OR where R is an alkyl of 1 to 10 carbon atoms or aralkyl of 7 to 15 carbon atoms.

12. A process of claim 11 wherein ##STR25## is in the p position and R is a branched chain alkyl group of 4 to 10 carbon atoms.

13. A process of claim 12 wherein R is t-butyl.

14. A process of claim 11 wherein R is benzyl.

15. A process of claim 11 wherein R is fluorenylmethyl.

8. A photoreactive polypeptide consisting essentially of a peptide chain containing at least one benzoylphenylalanine group in the chain having the formula:

##STR21## wherein ##STR22## is in the m or p position.

9. A polypeptide of claim 8 wherein ##STR23## is in the p-position.

16. A process for attaching a photoreactive polypeptide to a solid substrate comprising exposing a polypeptide of claim 8 to ultraviolet light of about 300-350 nanometers in the presence of a solid substrate having a reactive hydrogen.

17. A process of claim 16 wherein the solid substrate is a polystyrene, a polyolefin, an acrylic polymer, a polyamide or a protein.