Amide containing molecular imprinted polymers
DC CAFCFirst Claim
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1. A synthetic molecularly imprinted co-polymer prepared by steps consisting essentially of:
- copolymerizing (i) at least one monomer providing the synthetic molecularly imprinted copolymer with a free amide group, and (ii) at least one crosslinker, in the presence of (i) at least one polar organic solvent, and (ii) an enantiomer print molecule optionally having carboxylic acid functionality to form a co-polymerized composition;
substantially removing from the co-polymerized composition the enantiomeric print molecule to form the synthetic molecularly imprinted co-polymer;
wherein the print molecule, the monomer providing free amide, and the crosslinker are provided in a ratio sufficient to form specific noncovalent binding sites for the print molecule in the molecularly imprinted copolymer;
and wherein the molecularly imprinted copolymer exhibits toward racemic mixtures of the enantiomer print molecule in polar solvent an enantiomeric separation factor alpha of at least 2.03.
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Abstract
This invention relates to molecularly imprinted polymers (MIPs) using an amide as the hydrogen bonding functional group. The amide MIPs made according to this invention exhibited enantiomeric recognition of the imprinted species when evaluated by high performance liquid chromatography (HPLC) even in an aqueous phase. In addition, the amide MIPs demonstrated improved enantiomeric resolution and load capacity.
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31 Claims
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1. A synthetic molecularly imprinted co-polymer prepared by steps consisting essentially of:
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copolymerizing (i) at least one monomer providing the synthetic molecularly imprinted copolymer with a free amide group, and (ii) at least one crosslinker, in the presence of (i) at least one polar organic solvent, and (ii) an enantiomer print molecule optionally having carboxylic acid functionality to form a co-polymerized composition;
substantially removing from the co-polymerized composition the enantiomeric print molecule to form the synthetic molecularly imprinted co-polymer;
wherein the print molecule, the monomer providing free amide, and the crosslinker are provided in a ratio sufficient to form specific noncovalent binding sites for the print molecule in the molecularly imprinted copolymer;
and wherein the molecularly imprinted copolymer exhibits toward racemic mixtures of the enantiomer print molecule in polar solvent an enantiomeric separation factor alpha of at least 2.03. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 30, 31)
passing an enantiomeric mixture through a separation medium comprising the synthetic molecularly imprinted composition according to claim 1.
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31. A method according to claim 30, wherein the optional carboxylic acid functionality is present.
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28. A method for producing a synthetic molecularly imprinted copolymer consisting essentially of the steps of:
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copolymerizing (i) at least one monomer providing the synthetic molecularly imprinted copolymer with a free amide group, and (ii) at least one crosslinker;
in the presence of (i) at least one polar organic solvent, and (ii) an enantiomer print molecule optionally having carboxylic acid functionality, to form a co-polymerized composition;
substantially removing from the co-polymerized composition the enantiomeric print molecule to form the synthetic molecularly imprinted copolymer;
wherein the print molecule, the monomer providing free amide, and the crosslinker are provided in a ratio sufficient to form specific noncovalent binding sites for the print molecule in the molecularly imprinted copolymer;
and wherein the molecularly imprinted copolymer exhibits toward racemic mixtures of the enantiomer print molecule in polar solvent an enantiomeric separation factor alpha of at least 2.03. - View Dependent Claims (29)
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Specification