Proline chiral columns with broad chiral selectivity

• US 7,160,449 B2
• Filed: 11/12/2004
• Issued: 01/09/2007
• Est. Priority Date: 04/28/2003
• Status: Expired due to Fees

• Current Assignee: Tingyu Li
• Original Assignee: Vanderbilt University
• Inventors: Li, Tingyu
• Primary Examiner(s): Therkorn; Ernest G.
• Application Number:
  US10/987,238
• Publication Number:
  US 20050092686A1
• Time in Patent Office: 788 Days
• Field of Search: 210/635, 210/656, 210/659, 210/198.2, 210/502.1, 502/401, 502/402, 502/403, 502/404
• US Class Current: 210/198.2
• CPC Class Codes: B01D 15/3833 Chiral chromatography
• CPC Class Codes: B01J 20/289 bonded via a spacer
• CPC Class Codes: B01J 20/29 Chiral phases
• CPC Class Codes: B01J 20/3242 Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
• CPC Class Codes: C02F 1/42 by ion-exchange ion-exchange in general B01J

Abstract

A general chiral column with a multipleproline-based chiral stationary phase. Embodiments include chiral stationary phases of the following formula:

wherein n is any integer of 2 or greater, and analogs and isomers thereof.

Claims

1. A chiral stationary phase compound of the following formula:

2. The chiral stationary phase compound of claim 1, wherein n is any integer from 2 to 10.

3. The chiral stationary phase compound of claim 1, wherein the support is a silica support.

4. A chiral stationary phase compound of claim 1, of the following formula:

Fmoc-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica;

Fmoc-Pro-Pro-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica;

Fmoc-Pro-Pro-Pro-Pro-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica;

and analogs and isomers thereof.

5. A chiral stationary phase compound of the following formula:

6. The chiral stationary phase compound of claim 5, wherein the linker is of the following formula:

7. A process for separating enantiomeric mixtures by liquid chromatography, comprising:

providing a racemic mixture;

providing a chiral column that comprises an optically active multi-proline compound of the following formula;

8. The process of claim 7, wherein n in the optically active multi-proline compound is any integer from 2 to 10.

9. The process of claim 7, wherein the support is a silica support.

10. The process of claim 7, wherein the optically active multi-proline compound is of the following formula:

Fmoc-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica;

Fmoc-Pro-Pro-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica;

Fmoc-Pro-Pro-Pro-Pro-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica;

and analogs and isomers thereof.

11. The process of claim 7, wherein the linker is of the following formula:

12. The process of claim 7, wherein the linker is of the following formula: