# US 7,935,906 B2 · Separation and manipulation of a chiral object

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- Number: US 7,935,906 B2
- Document ID: US7935906B2
- Status: Granted
- Kind: B2
- Application number: 12/103,281
- Filed: 2008-04-15
- Published: 2008-10-23
- Granted: 2011-05-03
- Earliest claimed: 2007-04-17
- Assignees: Dynamic Connections, LLC
- Inventors: Osman Kibar; Mirianas Chachisvilis; Eugene Tu; Thomas H. Marsilje
- Web page: https://patentgrep.com/patent/US7935906B2

## CPC

- B03C 1/24: with material carried by travelling fields
- B03C 7/026: {using travelling or oscillating electric fields}
- C07B 57/00: Separation of optically-active compounds
- B03C: MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS (separating isotopes B01D59/00; combinations of magnetic or electrostatic separation with separation of solids by other means B03B, B07B)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Among other things, to cause directional motion of chiral objects in a mixture in a chamber, a field is rotated relative to a chamber to cause rotation of the chiral objects. The rotation of the objects caused them to move directionally based on their chirality.

## Claims

### Claim 1

A method for use in directional motion of chiral objects in a mixture, the method comprising, within a chamber that contains the chiral objects in the mixture, applying a field across the chamber that has a field direction and is rotating relative to the chamber to cause rotation of the chiral objects, each chiral object's axis of rotation lying at least partly within the chiral object itself, the rotations of the chiral objects causing a net directional motion of the chiral objects along the axis of rotation of the field.

### Claim 2 (depends on 1)

The method of claim 1 in which the field delivers insufficient energy to damage the chiral objects.

### Claim 3 (depends on 1)

The method of claim 1 in which the rotating occurs at a frequency that causes directional motion at a speed that is high enough to achieve a predetermined degree of separation of some of the chiral objects from the mixture at a predetermined concentration in no more than a predetermined amount of time.

### Claim 4 (depends on 1)

The method of claim 1 in which the field strength and the speed of rotation of the field are selected to achieve a predetermined level of efficiency of the directional motion.

### Claim 5 (depends on 1)

The method of claim 1 in which the electric field strength is lower than 105 V/m.

### Claim 6 (depends on 1)

The method of claim 1 in which the electric field has a rotational frequency higher than 100M rotations per second.

### Claim 7 (depends on 1)

The method of claim 1 in which the directional motion has a velocity of at least 0.1 angstrom per revolution.

### Claim 8 (depends on 1)

The method of claim 1 in which the chiral objects comprise chiral molecules.

### Claim 9 (depends on 8)

The method of claim 8 in which the molecules comprise stereoisomers.

### Claim 10 (depends on 9)

The method of claim 9 in which the stereoisomers comprise enantiomers.

### Claim 11 (depends on 9)

The method of claim 9 in which the stereoisomers comprise epimers.

### Claim 12 (depends on 1)

The method of claim 1 in which the chiral objects comprise aggregates of chiral or achiral molecules or both.

### Claim 13 (depends on 1)

The method of claim 1 in which the chiral objects comprise molecules having axial chirality.

### Claim 14 (depends on 8)

The method of claim 8 in which the molecules comprise drug molecules.

### Claim 15 (depends on 8)

The method of claim 8 in which the molecules comprise drug intermediate molecules.

### Claim 16 (depends on 9)

The method of claim 9 in which the stereoisomers have more than one stereocenter.

### Claim 17 (depends on 1)

The method of claim 1 in which the chiral objects are of one type.

### Claim 18 (depends on 1)

The method of claim 1 in which the chiral objects are of two types.

### Claim 19 (depends on 1)

The method of claim 1 in which the chiral objects are of more than two types.

### Claim 20 (depends on 1)

The method of claim 1 also comprising analyzing the chirality of the chiral objects based on the directional motion.

### Claim 21 (depends on 1)

The method of claim 1 also including detecting the presence or absence of chiral objects based on the directional motion.

### Claim 22 (depends on 1)

The method of claim 1 also including separating two or more types of chiral objects based on the directional motion.

### Claim 23 (depends on 22)

The method of claim 22 in which the chiral objects are separated into two groups.

### Claim 24 (depends on 22)

The method of claim 22 in which the chiral objects are separated into more than two groups.

### Claim 25 (depends on 22)

The method of claim 22 in which the chiral objects of the two or more types move in opposite directions.

### Claim 26 (depends on 22)

The method of claim 22 in which the chiral objects of the two or more types move in the same direction but at different average velocities.

### Claim 27 (depends on 22)

The method of claim 22 in which the chiral objects of the two or more types are separated in real-time.

### Claim 28 (depends on 22)

The method of claim 22 in which the chiral objects are separated as end-point.

### Claim 29 (depends on 1)

The method of claim 1 in which the field comprises an electric field.

### Claim 30 (depends on 1)

The method of claim 1 in which the field comprises a magnetic field.

### Claim 31 (depends on 1)

The method of claim 1 in which rotating the field relative to the chamber is performed in discrete steps.

### Claim 32 (depends on 1)

The method of claim 1 in which rotating the field relative to the chamber is performed continuously.

### Claim 33 (depends on 1)

The method of claim 1 in which rotating the field is performed around a stationary chamber.

### Claim 34 (depends on 1)

The method of claim 1 in which rotating the field comprises rotating the chamber relative to a field of fixed orientation.

### Claim 35 (depends on 1)

The method of claim 1 in which the mixture comprises a racemic mixture.

### Claim 36 (depends on 1)

The method of claim 1 in which rotating the field relative to the chamber is performed in successive angular positions around a central portion of the chamber.

### Claim 37 (depends on 1)

The method of claim 1 in which the field is applied from electrodes arranged on a peripheral wall of the chamber.

### Claim 38 (depends on 1)

The method of claim 1 in which the electric field is applied at successive angular orientations across the chamber at intervals that cause the electric field to rotate around the chamber with a selected rotational frequency profile.

### Claim 39 (depends on 38)

The method of claim 38 in which the rotational frequency profile is in at least one of the ranges of less than 1 kHz, 1 kHz to 10 kHz, 10 kHz to 100 kHz, 100 kHz to 1 MHz, 1 MHz to 10 MHz, 10 MHz to 100 MHz, 100 MHz to 1 GHz, 1 GHz to 10 GHz, or above 10 GHz.

### Claim 40 (depends on 38)

The method of claim 38 in which the rotational frequency is in the RF range.

### Claim 41 (depends on 38)

The method of claim 38 in which the rotational frequency is in the microwave range.

### Claim 42 (depends on 1)

The method of claim 1 in which the field is applied by an electromagnetic beam that is collinear with an axis of the chamber.

### Claim 43 (depends on 42)

The method of claim 42 in which the electromagnetic beam is circularly polarized.

### Claim 44 (depends on 42)

The method of claim 42 in which the rotational frequency profile is in the range of less than 1 kHz, 1 kHz to 10 kHz, 10 kHz to 100 kHz, 100 kHz to 1 MHz, 1 MHz to 10 MHz, 10 MHz to 100 MHz, 100 MHz to 1 GHz, 1 GHz to 10 GHz, or above 10 GHz.

### Claim 45 (depends on 42)

The method of claim 42 in which the rotational frequency is in the RF range.

### Claim 46 (depends on 42)

The method of claim 42 in which the rotational frequency is in the microwave range.

### Claim 47 (depends on 1)

The method of claim 1 in which the chiral objects are loaded into the chamber at a particular point along the chamber.

### Claim 48 (depends on 1)

The method of claim 1 in which the chiral objects are loaded into the chamber without regard to their entry point along the chamber.

### Claim 49 (depends on 1)

The method of claim 1 also comprising applying the field to cause a concentration of the chiral objects to reach a steady state.

### Claim 50 (depends on 1)

The method of claim 1 also comprising applying the field and then turning off the field before the concentration of the chiral objects reaches a steady state.

### Claim 51 (depends on 1)

The method of claim 1 in which a gradient of a concentration of the chiral objects in the mixture in the chamber comprises an exponential profile.

### Claim 52 (depends on 1)

The method of claim 1 in which a gradient of a concentration of the chiral objects in the mixture in the chamber comprises a linear profile.

### Claim 53 (depends on 1)

The method of claim 1 in which a gradient of a concentration of the chiral objects in the mixture in the chamber comprises a nonlinear profile.

### Claim 54 (depends on 1)

The method of claim 1 in which parameters associated with the directional motion are non-constant in the direction of the motion.

### Claim 55 (depends on 1)

The method of claim 1 also including associating a chiral label with the chiral objects.

### Claim 56 (depends on 55)

The method of claim 55 also including attaching entities to the chiral objects to increase dipole moments of the chiral objects.

### Claim 57 (depends on 55)

The method of claim 55 also including attaching entities to the chiral objects to increase a rotational/translational coupling factor.

### Claim 58 (depends on 1)

The method of claim 1 also including causing at least some of the chiral objects move collectively.

### Claim 59 (depends on 1)

The method of claim 1 in which the mixture comprises a fluid in which the chiral objects move.

### Claim 60 (depends on 59)

The method of claim 59 in which the fluid comprises a gas.

### Claim 61 (depends on 59)

The method of claim 59 in which the fluid comprises a polar solution.

### Claim 62 (depends on 59)

The method of claim 59 in which the fluid comprises a non-polar solution.

### Claim 63 (depends on 59)

The method of claim 59 in which the fluid comprises a high pressure fluid.

### Claim 64 (depends on 59)

The method of claim 59 in which the fluid is in a supercritical phase.

### Claim 65 (depends on 59)

The method of claim 59 in which the fluid's composition or properties are controlled.

### Claim 66 (depends on 61)

The method of claim 61 in which the chiral objects exhibit a smaller dipole moment than molecules of the polar solution.

### Claim 67 (depends on 59)

The method of claim 59 in which the directional motion is achieved by rotating molecules of the fluid to impart angular momentum on the objects to cause them to rotate.

### Claim 68 (depends on 1)

The method of claim 1 in which the directional motion occurs within a flow of the mixture.

### Claim 69 (depends on 1)

The method of claim 1 also including causing the mixture to flow in a manner that counters the directional motion of the chiral objects.

### Claim 70 (depends on 1)

The method of claim 1 in which the applied field has a profile other than constant along a direction of the chamber.

### Claim 71 (depends on 70)

The method of claim 70 in which the direction is along a length of the chamber or orthogonal to a length of the chamber.

### Claim 72 (depends on 1)

The method of claim 1 also including controlling the directional motion using feedback.

### Claim 73 (depends on 1)

The method of claim 1 also including monitoring an outcome of the directional motion.

### Claim 74 (depends on 1)

The method of claim 1 also comprising allowing or managing multiple runs in series.

### Claim 75 (depends on 1)

The method of claim 1, in which the chamber contains a chemical matrix.

### Claim 76 (depends on 1)

The method of claim 1 also including using a result in analytical chemistry.

### Claim 77 (depends on 1)

The method of claim 1 also including using a result in drug discovery.

### Claim 78 (depends on 1)

The method of claim 1 also including using a result in drug development.

### Claim 79 (depends on 1)

The method of claim 1 also including using a result in drug manufacture.

### Claim 80 (depends on 1)

The method of claim 1 also including using a result in process monitoring.

### Claim 81 (depends on 1)

The method of claim 1 also including using a result in medical diagnostics.

### Claim 82 (depends on 1)

The method of claim 1 also including using a result in fine chemical or synthetic intermediate manufacture.

### Claim 83 (depends on 1)

The method of claim 1 also including using a result in agrochemicals.

### Claim 84 (depends on 1)

The method of claim 1 also including using a result in petrochemicals.

### Claim 85 (depends on 1)

The method of claim 1 also including using a result in flavors and fragrances.

### Claim 86 (depends on 1)

The method of claim 1 in which the chiral objects comprise achiral objects with chiral labels attached.

### Claim 87 (depends on 1)

The method of claim 1 in which the chiral objects comprise unknown molecules.

### Claim 88 (depends on 1)

The method of claim 1 in which the chiral objects comprise known molecules.

### Claim 89 (depends on 1)

The method of claim 1 also including using a result to quantify a specific property of the chiral object.

### Claim 90 (depends on 89)

The method of claim 89 in which the specific property of the chiral object comprises its propeller propulsion efficiency.

### Claim 91 (depends on 89)

The method of claim 89 in which the specific property of the chiral object comprises its absolute configuration.

### Claim 92 (depends on 89)

The method of claim 89 in which the specific property of the chiral object comprises its presence or absence in the solution.

### Claim 93 (depends on 89)

The method of claim 89 in which the specific property of the chiral object comprises the magnitude or the orientation of its dipole moment.

### Claim 94 (depends on 1)

The method of claim 1 in which the system or the resulting separations are used in electro-rotary chemistry.

### Claim 95 (depends on 94)

The method of claim 94 in which the electro-rotary chemistry comprises chiral synthesis.

### Claim 96 (depends on 94)

The method of claim 94 in which the electro-rotary chemistry comprises reactions or applications involving catalysis.

### Claim 97 (depends on 94)

The method of claim 94 in which the electro-rotary chemistry comprises the study or the detection of molecular interactions.

### Claim 98 (depends on 8)

The method of claim 8 in which the spatial concentration profile of the chiral molecules is changed to manipulate the chemical reactions involving them.

### Claim 99 (depends on 8)

The method of claim 8 in which the system is used to separate or purify the chiral molecules from achiral impurities in the solution.

### Claim 100 (depends on 86)

The method of claim 86 in which the chiral labels are self-assembled.

### Claim 101 (depends on 86)

The method of claim 86 in which the chiral labels are self-activated.

### Claim 102 (depends on 86)

The method of claim 86 in which the chiral labels are pre-activated.

### Claim 103 (depends on 86)

The method of claim 86 in which the achiral objects comprise molecules, such as DNA, RNA, peptides, proteins or amino acids.

### Claim 104 (depends on 86)

The method of claim 86 in which the achiral objects comprise living organisms, such as viruses, bacteria or cells.

### Claim 105 (depends on 86)

The method of claim 86 in which more than one type of chiral label is used for multiplex assays.

### Claim 106 (depends on 86)

The method of claim 86 in which chiral labels are used for debulking or enriching sample matrices.

### Claim 107 (depends on 86)

The method of claim 86 in which the chiral labels comprise propeller entities.

### Claim 108 (depends on 107)

The method of claim 107 in which the propeller entities are conjugated to antibodies or nucleic acids.

### Claim 109 (depends on 107)

The method of claim 107 in which the propeller entities comprise at least two components.

### Claim 110 (depends on 86)

The method of claim 86 in which the chiral labels comprise aptamers.

### Claim 111 (depends on 110)

The method of claim 110 in which the aptamers become chiral or reverse their chirality upon binding to achiral objects.