Chiral columns with broad chiral selectivity

• US 7,141,160 B2
• Filed: 04/28/2004
• Issued: 11/28/2006
• 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:
  US10/833,602
• Publication Number:
  US 20040226889A1
• Time in Patent Office: 944 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

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 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. The chiral stationary phase compound of claim 1, wherein the linker is an N-alkylamino group.

5. The chiral stationary phase compound of claim 4, wherein the linker is an N-methylamino group.

6. The chiral stationary phase compound of claim 4, wherein the linker is a 6-methylaminohexanoic acid group.

7. The chiral stationary phase of a compound of claim 1, wherein the end-capping group is a Piv, Fmoc, Boc, Cbz, Aca, Tapa, Dmb, or a Tpa.

8. The chiral stationary phase of claim 1, wherein the linker is of the following formula:

9. The chiral stationary phase compound of claim 1, wherein the linker is of the following formula:

10. The chiral stationary phase compound of claim 1, wherein the end-capping group is a Piv, Fmoc, Cbz, Aca, Tapa, Dub, or Tpa group.

11. The chiral stationary phase compound of claim 1, of the following formula:

13. A chiral column, comprising a chiral stationary phase compound of claim 1.

12. An optically active proline derivative of the formula: