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US4582875A
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Method of activating hydroxyl groups of a polymeric carrier using 2-fluoro-1-methylpyridinium toluene-4-sulfonate
Assignee: Unisyn Fibertec Corp
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Filing: 1984-12-07
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Granted: 1986-04-15
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Expires: 2004-12-07
Abstract
Abstract Organic ligands containing at least one primary or secondary amino group or sulfhydryl group are coupled to a polymeric carrier containing at least one hydroxyl group, by activating the polymeric carrier by treatment with 2-fluoro-1-methylpyridinium toluene-4-sulfonate and reacting the activated polymeric carrier with the organic ligand which is thereby bonded directly to a carbon atom of the polymeric carrier. The polymeric carrier can, for example, be a possibly cross-linked polysaccharide and the organic ligand is preferably a biologically active material such as a drug or protein. The coupling product is an affinity matrix which can be used for affinity purification, covalent chromatography and reversible or irreversible covalent immobilization of biologically active molecules. The coupling method can be performed under mild conditions not damaging sensitive molecules.
Inventors
- 👤 That T. Ngo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:09
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/30; Y; Y10; Y10S; Y10S530/00; Y10S530/81; Y10S530/812; Y10S530/815; Y10S530/816
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
53 words
A process for activating a hydroxyl group of a polymeric substance containing at least one hydroxyl group comprising: reacting a polymeric substance containing at least one hydroxyl group with 2-fluoro-1-methylpyridinium toluene-4-sulfonate, and recovering a polymeric product wherein at least some of the hydroxyl groups of the polymer have been converted to 1-methyl-2-pyridoxy groups.
Claim 2
Dependent Claim
53 words
A process for activating a hydroxyl group of a polymeric substance containing at least one hydroxyl group comprising: reacting a polymeric substance containing at least one hydroxyl group with 2-fluoro-1-methylpyridinium toluene-4-sulfonate, and recovering a polymeric product wherein at least some of the hydroxyl groups of the polymer have been converted to 1-methyl-2-pyridoxy groups.
Claim 3
Dependent Claim
48 words
A process according to claim 1 wherein the reaction is conducted in the presence of a slight excess of a tertiary amine and in a dry polar organic solvent at a temperature in the range of about 22°-35° C. for a period of about one to fifteen minutes.
Claim 4
Dependent Claim
49 words
A process according to claim 1 wherein the separated 1-methyl-2-pyridoxy substituted polymer is purified and stabilized by washing with a dilute acid and the resulting purified and stabilized polymer containing 1-methyl-2-pyridoxy groups is stored in a dilute acid or dried at a temperature of about 4° C. or lower.
Claim 5
Dependent Claim
19 words
A process according to claim 1 wherein the 1-methyl-2-pyridoxy substituted polymer is washed with 2 mM HCl and dried.
Claim 6
Dependent Claim
15 words
A process according to claim 1 wherein said hydroxyl group containing polymer is a polysaccharide.
Claim 7
Dependent Claim
12 words
A process according to claim 5 wherein said polysaccharide is a dextran.
Claim 8
Dependent Claim
13 words
A process according to claim 5 wherein said polysaccharide is a cross-linked dextran.
Claim 9
Dependent Claim
12 words
A process according to claim 5 wherein said polysaccharide is an agarose.
Claim 10
Dependent Claim
13 words
A process according to claim 5 wherein said polysaccharide is a cross-linked agarose.
Claim 11
Dependent Claim
16 words
A process according to claim 5 wherein said polysaccharide is in the form of a gel.
Claim 12
Dependent Claim
11 words
A process according to claim 5 wherein said polysaccharide is cellulose.
Claim 13
Dependent Claim
12 words
A process according to claim 1 wherein said polymer is polyethylene glycol.
Claim 14
Dependent Claim
12 words
A process according to claim 1 wherein said polymer is polyvinyl alcohol.
Claim 15
Dependent Claim
14 words
A process according to claim 1 wherein said polymer is a polyhydroxyethyl methyl acrylate.
Claim 16
Dependent Claim
32 words
A process according to claim 1 wherein said polymer comprises silica particles, to the surface of which have been bonded groups containing at least one hydroxyl group bonded to a carbon atom.
Claim 17
Dependent Claim
31 words
An activated polymer capable of forming covalent linkages with a nucleophilic ligand which comprises: a hydroxyl-containing polymer wherein at least some of the hydroxyl groups have been converted to 1-methyl-2-pyridoxy groups.
Claim 18
Dependent Claim
31 words
An activated polymer capable of forming covalent linkages with a nucleophilic ligand which comprises: a hydroxyl-containing polymer wherein at least some of the hydroxyl groups have been converted to 1-methyl-2-pyridoxy groups.
Claim 19
Dependent Claim
102 words
A process of covalently binding: (a) an organic ligand that contains at least one substituent selected from the group consisting of primary amino groups, secondary amino groups and sulfhydryl groups; directly to a: (b) polymeric substance containing at least one hydroxyl group; comprising the steps of: (1) first forming a reactive derivative by reacting (i) 1-fluoro-2-methylpyridinium toluene 4-sulfonate with (ii) a polymeric substance containing at least one hydroxyl group, wherein at least one reacting hydroxyl group is bonded to carbon atoms in the polymeric substance and then (2) reacting said reactive derivative directly with the organic ligand as set forth in (a).
Claim 20
Dependent Claim
102 words
A process of covalently binding: (a) an organic ligand that contains at least one substituent selected from the group consisting of primary amino groups, secondary amino groups and sulfhydryl groups; directly to a: (b) polymeric substance containing at least one hydroxyl group; comprising the steps of: (1) first forming a reactive derivative by reacting (i) 1-fluoro-2-methylpyridinium toluene 4-sulfonate with (ii) a polymeric substance containing at least one hydroxyl group, wherein at least one reacting hydroxyl group is bonded to carbon atoms in the polymeric substance and then (2) reacting said reactive derivative directly with the organic ligand as set forth in (a).
Claim 21
Dependent Claim
46 words
A product of coupling an organic ligand that contains at least one substituent selected from the group consisting of primary amino groups, secondary amino groups, and sulfhydryl groups to a polymeric substance containing at least one hydroxyl group; prepared according to the process of claim 17.
Claim 22
Dependent Claim
12 words
A process according to claim 18 wherein said organic ligand is N,ε-2,4-dinitrophenyl-L-lysine.
Claim 23
Dependent Claim
12 words
A process according to claim 18 wherein said organic ligand is tobramycin.
References Cited (Backward Citations)
US4195128A
Cited
US4415665A
Cited
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