Separation of amino acids, amino-acid-based monomer, and process for the preparation thereof, as well as polymer material and process for the preparation thereof

• US 5,541,342 A
• Filed: 09/12/1994
• Issued: 07/30/1996
• Est. Priority Date: 12/20/1991
• Status: Expired due to Fees

• Current Assignee: Bio-Swede AB, Cultor OY (International Flavors & Fragrances Incorporated), Danisco Finland Oy (International Flavors & Fragrances Incorporated)
• Original Assignee: Bio-Swede AB, Cultor OY (International Flavors & Fragrances Incorporated)
• Inventors: Hietaniemi, Lauri, Ekberg, Bj orn, Korhonen, Pirjo
• Primary Examiner(s): RICHTER, JOHANN R
• Application Number:
  US08/244,726
• Time in Patent Office: 687 Days
• Field of Search: 548/532, 548/402
• US Class Current: 548/532
• CPC Class Codes: B01J 20/268 Polymers created by use of a template, e.g. molecularly imprinted polymers
• CPC Class Codes: C07C 227/40 Separation; Purification
• CPC Class Codes: 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
• CPC Class Codes: G01N 2600/00 Assays involving molecular imprinted polymers/polymers created around a molecular template

Abstract

A process for separating a selected amino acid (enantiomer) from a mixture of different compounds including other amino acids is disclosed, in which process the mixture is contacted with a polymer material which is composed of cross-linked, amino-acid-based monomer units, said polymer material containing a molecular print of the selected amino acid. In the molecular print there is also bound a diastereomeric complex between the selected amino acid (enantiomer), a divalent metallic ion and the amino-acid-based monomer unit. Also the amino-acid-based monomer unit and a process for preparation thereof, as well as a polymer material composed of the amino-acid-based monomer unit and a process for the preparation thereof are disclosed.

Claims

1. A method for preparing a molecular print polymer for adsorbing an enantiomer of a chiral nonderivatized amino acid, comprising:

(A) preparing a diastereomeric complex between a monomer unit comprising an amino acid moiety, an enantiomer of a chiral nonderivatized amino acid, and a divalent metallic ion capable of forming a complex between said monomer unit and said enantiomer;

(B) polymerizing the monomer moieties of said complex in the presence of a crosslinking agent; and

(C) removing said amino acid from said polymerized complex, thereby obtaining said molecular print polymer.

2. The method as claimed in claim 1, wherein said chiral nonderivatized amino acid is naturally occurring.

3. The method as claimed in claim 1, wherein said chiral nonderivatized amino acid is synthetic.

4. The method as claimed in claim 1, wherein said monomer unit comprising an amino acid moiety is selected from the group consisting of N-methacrylamidomethyl-L-proline and N-methacrylamidomethyl-D-proline.

5. The method as claimed in claim 1, wherein said divalent metallic ion is selected from the group consisting of copper (II), manganese (II), iron (II), cobalt (II), zinc (II), cadmium (II), and nickel (II).

6. A molecular print polymer produced by the process of claim 1.

7. A molecular print polymer comprising:

(A) a crosslinked polymerized monomer comprising an amino acid moiety;

(B) a divalent metallic ion capable of forming a complex between said amino acid moiety of said monomer and an enantiomer of a chiral nonderivatized amino acid;

wherein said polymer comprises affinity seats for said enantiomer, formed when said monomer is polymerized and crosslinked as a complex of said enantiomer and said divalent metallic ion.

8. The molecular print polymer as claimed in claim 7, wherein said monomer unit comprising an amino acid moiety is selected from the group consisting of N-methacrylamidomethyl-L-proline and N-methacrylamidomethyl-D-proline.

9. The molecular print polymer as claimed in claim 7, wherein said chiral nonderivatized amino acid is naturally occurring.

10. The molecular print polymer as claimed in claim 7, wherein said chiral nonderivatized amino acid is synthetic.

11. The molecular print polymer as claimed in claim 7, wherein said divalent metallic ion is selected from the group consisting of copper (II), manganese (II), iron (II), cobalt (II), zinc (II), cadmium (II), and nickel (II).

12. A process for separating an enantiomer of a chiral nonderivatized amino acid from a mixture thereof, comprising:

(A) contacting a mixture comprising an enantiomer of a chiral nonderivatized amino acid with a molecular print polymer comprising;

(1) a crosslinked polymerized monomer comprising an amino acid moiety;

(2) a divalent metallic ion capable of forming a complex between said amino acid moiety of said monomer and an enantiomer of a chiral nonderivatized amino acid;

wherein said polymer comprises affinity seats for said enantiomer, formed when said monomer is polymerized and crosslinked as a complex of said enantiomer and said divalent metallic ion;

wherein said contacting occurs under conditions sufficient for said enantiomer to form a complex with said divalent metallic ion of said polymer; and

(B) removing the enantiomer depleted mixture from contact with the polymer.

13. The process as claimed in claim 12, wherein said monomer unit comprising an amino acid moiety is selected from the group consisting of N-methacrylamidomethyl-L-proline and N-methacrylamidomethyl-D-proline.

14. The process as claimed in claim 12, wherein said chiral nonderivatized amino acid is naturally occurring.

15. The process as claimed in claim 12, wherein said chiral nonderivatized amino acid is synthetic.

16. The process as claimed in claim 12, wherein said divalent metallic ion is selected from the group consisting of copper (II), manganese (II), iron (II), cobalt (II), zinc (II), cadmium (II), and nickel (II).

17. The process as claimed in claim 12, wherein said enantiomer of said chiral amino acid is selected from the group consisting of D-proline and L-serine.

18. An amino acid-based monomer selected from the group consisting of N-methacrylamidomethyl-L-proline and N-methacrylamidomethyl-D-proline.

19. A method for preparing N-methacrylamidomethyl-L-proline and N-methacrylamidomethyl-D-proline, comprising condensing L-proline or D-proline, formalin, and methacrylamide under alkaline conditions.