# US 6,296,768 B1 · Separating materials for chromatography and electrophoresis applications comprising regiodefined functionalised cyclodextrins chemically bonded to a support via urethane functionalities

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- Number: US 6,296,768 B1
- Document ID: US6296768B1
- Status: Granted
- Kind: B1
- Application number: 09/442,266
- Filed: 1999-11-18
- Granted: 2001-10-02
- Earliest claimed: 1997-08-27
- Assignees: National University of Singapore
- Inventors: Siu Choon Ng; Lifong Zhang; Chi Bun Ching
- Web page: https://patentgrep.com/patent/US6296768B1

## CPC

- B01D 15/3833: {Chiral chromatography}
- B01J 20/286: Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J 20/289: bonded via a spacer
- B01J 20/29: Chiral phases
- B01J 20/3204: {Inorganic carriers, supports or substrates}
- B01J 20/3217: {Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond}
- B01J 20/3219: {involving a particular spacer or linking group, e.g. for attaching an active group}
- B01J 20/3227: {by end-capping, i.e. with or after the introduction of functional or ligand groups}
- B01J 20/3246: {having a well defined chemical structure}
- B01J 20/3251: {comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulphur}
- B01J 20/3255: {comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. heterocyclic or heteroaromatic structures}
- B01J 20/3257: {the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such}
- B01J 20/3259: {comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom}
- B01J 20/3263: {comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. an heterocyclic or heteroaromatic structure}
- G01N 27/44747: {Composition of gel or of carrier mixture}
- B01J 2220/54: Sorbents specially adapted for analytical or investigative chromatography
- B01J 2220/58: Use in a single column
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

Novel and improved chiral stationary phases (CSP) materials comprising a support and completely regiodefined derivitised cyclodextrin chemically bonded via single or double urethane linkage(s) universally applicable in HPLC, LC, TLC, and CCE are obtained using a process based on the almost quantitative reaction of pre-synthesized regiodefined per-functionalized mono- or di- azidocyclodextrin with primary amines.

## Claims

### Claim 1

A method for chromatographic or electrophoretic separation of a mixture comprising, respectively, contacting a sample comprising said mixture with or applying a sample comprising said mixture to a separation support material, said separation support material being one produced by a process comprising any one of the following steps:
(a) reacting a regiodefined mono-azido perfunctionalized cyclodextrin or a regiodefined di-azido perfunctionalized cyclodextrin with a support that carries free NH2 groups;
(b) reacting a regiodefined mono-azido perfunctionalized cyclodextrin or a regiodefined di-azido perfunctionalized cyclodextrinwith an alkenyl amine to produce a product comprising a C═C group linked to a side chain via a urethane linkage, further hydrosilating the C═C group of said product with an active silane, and chemically immobilizing the product onto the surface of a support;
(c) reacting a regiodefined mono-azido perfunctionalized cyclodextrin or a regiodefined di-azido perfunctionalized cyclodextrin with an aminosilane containing at least one further reactive group to form a product, and chemically immobilizing the product onto a surface of a support; and
(d) reducing a regiodefined mono-azido perfunctionalized cyclodextrin or a regiodefined di-azido perfunctionalized cyclodextrin to a monoamino or diamino perfunctionalized cyclodextrin, and then anchoring the mono- or diamino perfunctionalized cyclodextrin onto the surface of a support by a coupling reagent, and, in the case of electrophoretic separation, applying an electric field.

### Claim 2 (depends on 1)

The method for separation of claim 1, which comprises method for chromatographic separation of a mixture.

### Claim 3 (depends on 2)

The method of claim 2, wherein said mixture comprises a mixture of enantiomers of a compound.

### Claim 4 (depends on 1)

The method for separation of claim 1, which comprises method for electrophoretic separation of a mixture.

### Claim 5 (depends on 4)

The method of claim 4, wherein said mixture comprises a mixture of enantiomers of a compound.