IP Library Granted Patent US 9,726,596
Granted Patent B2
US 9,726,596 · App. 14/539,790 · Granted Aug 8, 2017

Configurational chirality based separation

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Quick Facts
Patent No.
US 9,726,596
App. No.
14/539,790
Granted
Aug 8, 2017
Kind
B2
Abstract

A method of determining the relative concentrations of enantiomeric forms of a compound in an enantiomeric mixture includes combining the enantiomeric mixture with carbon nanotubes or graphene to form a carbon-enantiomer mixture, exposing the mixture to a monochromatic polarized light, and analyzing reflected polarized light from the mixture using a differential analyzer.

Claims (31)

1. A method of determining the relative concentrations of each of two enantiomeric forms of a compound in an enantiomeric mixture, the method comprising:

combining the enantiomeric mixture with carbon nanotubes or graphene to form a carbon-enantiomer mixture;

exposing the carbon-enantiomer mixture to a monochromatic polarized light;

analyzing reflected monochromatic polarized light from the carbon-enantiomer mixture using a differential analyzer; and

determining the relative concentrations of each of the two enantiomeric forms of the compound in the enantiomeric mixture.

2. The method of claim 1 , wherein the analyzing step comprises:

observing a differential binding parameter of the carbon-enantiomer mixture in a circular dichroism experiment; and

comparing the differential-binding parameter of the carbon-enantiomer mixture to a known differential-binding parameter curve of known concentration carbon-enantiomer mixtures to determine the relative concentrations of the enantiomeric forms in the enantiomeric mixture.

3. The method of claim 1 , wherein the combining comprises sonicating the enantiomeric mixture with the carbon nanotubes or the graphene.

4. The method of claim 3 , wherein the enantiomeric mixture is sonicated with the carbon nanotubes.

5. The method of claim 4 , wherein the carbon nanotubes are in a zigzag conformation.

6. The method of claim 3 , wherein the enantiomeric mixture is sonicated with the graphene.

7. The method of claim 3 , wherein the enantiomeric mixture and the carbon nanotubes or the graphene are combined in water.

8. The method of claim 1 , wherein the method comprises combining the enantiomeric mixture with the graphene to form the carbon-enantiomer mixture.

9. The method of claim 8 , wherein the combining comprises sonicating the enantiomeric mixture with the graphene.

10. A method of determining a concentration of zigzag conformation single-walled carbon nanotubes in a solution, the method comprising:

contacting the solution comprising single-walled carbon nanotubes with a solution comprising an enantiomerically pure compound to form a mixed solution;

measuring a change in ellipticity of the solution as a function of wavelength in a circular dichroism experiment;

comparing the change in ellipticity of the solution to a change in ellipticity of standardized concentration solutions of the zigzag conformation single-walled carbon nanotubes; and

determining the concentration of the zigzag conformation single-walled carbon nanotubes in the solution.

11. The method of claim 10 , wherein the enantiomerically pure compound is enantiomerically pure tryptophan.

12. A method of chiral separation comprising:

contacting a first solution with a column, wherein the first solution comprises a mixture of a first enantiomer and a second enantiomer, and the column consists essentially of single-walled carbon nanotubes, multi-walled carbon nanotubes, or graphene;

eluting from the column a second solution comprising an elevated concentration of the first enantiomer as compared to a concentration of the first enantiomer in the first solution.

13. The method of claim 12 , wherein the first enantiomer is a dextrorotary enantiomer.

14. The method of claim 12 , wherein the first enantiomer is a levorotatory enantiomer.

15. The method of claim 12 , wherein the first enantiomer is D-tryptophan and the second enantiomer is L-tryptophan.

16. The method of claim 12 , wherein the column is a liquid chromatography column, a high pressure liquid chromatography column, or a flow cytometry column.

17. The method of claim 12 , wherein the column comprises single-walled carbon nanotubes.

18. The method of claim 17 , wherein the single-walled carbon nanotubes have a zigzag configuration.

19. The method of claim 12 , wherein the first solution and the second solution comprise water, acetone, toluene, and carbon tetrachloride.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jul 31, 2019
From: CRESTLINE DIRECT FINANCE, L.P.
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 049924/0794 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2014
From: DASGUPTA, ANJAN KR.; BHATTACHARYYA, TAMOGHNA; ROY, SARITA
To: UNIVERSITY OF CALCUTTA
Reel/Frame 034248/0031 →