Polyaza[n]paracyclophanes as synthetic models of Zn containing enzymes. The role of a non coordinated nitrogen atom in the proximity of the metal

被引:33
作者
Altava, B
Burguete, MI
Luis, SV
Miravet, JF
GarciaEspana, E
Marcelino, V
Soriano, C
机构
[1] ESTEC, DEPT ORGAN & INORGAN CHEM, CASTELLO DE LA PLANA 12080, SPAIN
[2] UNIV VALENCIA, DEPT INORGAN & ORGAN CHEM, E-46100 BURJASSOT, SPAIN
关键词
D O I
10.1016/S0040-4020(97)00144-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,6,9,13-Tetraaza[14]paracyclophane (3, B323) represents a simple model for Zn containing enzymes like HCAII which possess additional reactive groups in the proximity of the metal center. The Zn2+.3 complex shows notable catalytic activity for the hydrolysis of p-nitrophenyl acetate. Structural modifications of 3 which affect to the non coordinated nitrogen atom greatly modify the catalytic activity of the receptor. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4751 / 4762
页数:12
相关论文
共 61 条
[1]  
ALTAVA B, IN PRESS SUPRAMOLECU
[2]   POLYAZACYCLOPHANES - 2,6,9,13-TETRAAZA[14]PARACYCLOPHANE AS A CATIONIC AND ANIONIC RECEPTOR [J].
ANDRES, A ;
BURGUETE, MI ;
GARCIAESPANA, E ;
LUIS, SV ;
MIRAVET, JF ;
SORIANO, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (04) :749-755
[3]  
AQVIST J, 1993, J AM CHEM SOC, V115, P631
[4]   REMARKABLE SHAPE SELECTIVITY IN THE MOLECULAR RECOGNITION OF CARBOXYLATE ANIONS IN AQUEOUS-SOLUTION [J].
BENCINI, A ;
BIANCHI, A ;
BURGUETE, MI ;
GARCIAESPANA, E ;
LUIS, SV ;
RAMIREZ, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1919-1920
[5]   AN EFFICIENT SYNTHESIS OF POLYAZA[N]PARACYCLOPHANES [J].
BENCINI, A ;
BURGUETE, MI ;
GARCIAESPANA, E ;
LUIS, SV ;
MIRAVET, JF ;
SORIANO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4749-4753
[6]  
Bertini I., 1994, Bioinorganic Chemistry, DOI 10/BioinCh_chapter9.pdf
[7]  
BERTINI L, 1986, ZINC ENZYMES
[8]   PROTONATION TENDENCIES OF AZAPARACYCLOPHANES - A THERMODYNAMIC AND NMR-STUDY [J].
BIANCHI, A ;
ESCUDER, B ;
GARCIAESPANA, E ;
LUIS, SV ;
MARCELINO, V ;
MIRAVET, JF ;
RAMIREZ, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (06) :1253-1259
[9]   PHOSPHATE ESTER CLEAVAGE CATALYZED BY BIFUNCTIONAL ZINC-COMPLEXES - COMMENTS ON THE P-NITROPHENYL ESTER SYNDROME [J].
BRESLOW, R ;
SINGH, S .
BIOORGANIC CHEMISTRY, 1988, 16 (04) :408-417
[10]   SYNTHESIS OF SOME POLYIMIDAZOLE LIGANDS RELATED TO ZINC ENZYMES [J].
BRESLOW, R ;
HUNT, JT ;
SMILEY, R ;
TARNOWSKI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (16) :5337-5342