Molecular imprinting of carboxylic acids employing novel functional macroporous polymers

被引:80
作者
Spivak, D [1 ]
Shea, KJ [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1021/jo982118s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Imprinted network polymers incorporating basic functional groups were developed to assess the binding and specificity of carboxylic acids. The binding affinities were determined using t-BOC-phenylalanine and 2-phenylbutyric acid as templates and substrates. Chiral. selectivity for the enantiomers of t-BOC-phenylalanine was found for polymers incorporating adenine or 2-aminopyridine functionality. Chiral selectivity in the case of (R)-(-)-2-phenylbutyric acid was found for the polymer utilizing N-(2-aminoethyl) methacrylamide as the functional monomer. Optimization of binding was achieved by changing polymerization conditions (thermal versus photochemical polymerization, monomer:template ratio) for t-BOC-phenylalanine imprinted polymers employing the N-(2-aminopyridine) methacrylamide monomer.
引用
收藏
页码:4627 / 4634
页数:8
相关论文
共 41 条
[1]   IMPRINTING OF AMINO-ACID DERIVATIVES IN MACROPOROUS POLYMERS [J].
ANDERSSON, L ;
SELLERGREN, B ;
MOSBACH, K .
TETRAHEDRON LETTERS, 1984, 25 (45) :5211-5214
[2]   DESIGNED CATALYSTS - A SYNTHETIC NETWORK POLYMER THAT CATALYZES THE DEHYDROFLUORINATION OF 4-FLUORO-4-(P-NITROPHENYL)BUTAN-2-ONE [J].
BEACH, JV ;
SHEA, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) :379-380
[3]   ANION COORDINATION CHEMISTRY - POLYGUANIDINIUM SALTS AS ANION COMPLEXONES [J].
DIETRICH, B ;
FYLES, DL ;
FYLES, TM ;
LEHN, JM .
HELVETICA CHIMICA ACTA, 1979, 62 (08) :2763-2787
[4]   MOLECULAR RECOGNITION - BIS-ACYLGUANIDINIUMS PROVIDE A SIMPLE FAMILY OF RECEPTORS FOR PHOSPHODIESTERS [J].
DIXON, RP ;
GEIB, SJ ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :365-366
[5]   CHIRAL RECOGNITION OF AROMATIC CARBOXYLATE ANIONS BY AN OPTICALLY-ACTIVE ABIOTIC RECEPTOR CONTAINING A RIGID GUANIDINIUM BINDING SUBUNIT [J].
ECHAVARREN, A ;
GALAN, A ;
LEHN, JM ;
DEMENDOZA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4994-4995
[6]   ANION-RECEPTOR MOLECULES - SYNTHESIS OF A CHIRAL AND FUNCTIONALIZED BINDING SUBUNIT, A BICYCLIC GUANIDINIUM GROUP DERIVED FROM L-ASPARAGINE OR D-ASPARAGINE [J].
ECHAVARREN, A ;
GALAN, A ;
DEMENDOZA, J ;
SALMERON, A ;
LEHN, JM .
HELVETICA CHIMICA ACTA, 1988, 71 (04) :685-693
[7]   MOLECULAR RECOGNITION - HYDROGEN-BONDING RECEPTORS THAT FUNCTION IN HIGHLY COMPETITIVE SOLVENTS [J].
FAN, E ;
VANARMAN, SA ;
KINCAID, S ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :369-370
[8]   DIRECT ENANTIOSEPARATION OF BETA-ADRENERGIC BLOCKERS USING A CHIRAL STATIONARY PHASE PREPARED BY MOLECULAR IMPRINTING [J].
FISCHER, L ;
MULLER, R ;
EKBERG, B ;
MOSBACH, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9358-9360
[9]   MOLECULAR RECOGNITION - A REMARKABLY SIMPLE RECEPTOR FOR THE SELECTIVE COMPLEXATION OF DICARBOXYLIC-ACIDS [J].
GARCIATELLADO, F ;
GOSWAMI, S ;
CHANG, SK ;
GEIB, SJ ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7393-7394
[10]  
Guyot A., 1982, PROG POLYM SCI, V8, P277, DOI [10.1016/0079-6700(82)90002-8., DOI 10.1016/0079-6700(82)90002-8]