Guest-selective binding of Z amino acids by a strapped metalloporphyrin receptor with a hydrogen-bonding capability

被引:24
作者
Zheng, JY [1 ]
Konishi, K [1 ]
Aida, T [1 ]
机构
[1] UNIV TOKYO,GRAD SCH ENGN,DEPT CHEM & BIOTECHNOL,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/S0040-4020(97)00611-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In competitive complexation of Z-amino acids (N-benzyloxycarbonyl-amino acids) in CDCl3, a synthetic receptor such as zinc N-methylmesoporphyrin II having a xylylenediamido strap (1a) preferred Z-glycine over other Z-amino acids, where an excellent selectivity (> 90 %) was achieved when Z-beta-alanine, Z-sarcosine, Z-leucine, or Z-proline was the competitor. In contrast, in competitive binding of Z-amino acid anions in a CHCl3/water biphasic system, 1a preferred substrates with hydrophobic side chains. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:9115 / 9122
页数:8
相关论文
共 20 条
[1]   THE CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL GROUP ARRAYS .19. GENERAL EFFECTS OF BINDING-SITE WATER EXCLUSION ON HYDROGEN-BOND BASED MOLECULAR RECOGNITION SYSTEMS - A CLOSED BINDING-SITE IS LESS AFFECTED BY ENVIRONMENTAL-CHANGES THAN AN OPEN SITE [J].
ADRIAN, JC ;
WILCOX, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1398-1403
[2]   TRANSPORT IN ORGANIC-CHEMISTRY .1. TRANSPORT OF AMINO-ACIDS THROUGH ORGANIC LIQUID MEMBRANES [J].
BEHR, JP ;
LEHN, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (18) :6108-6110
[3]   TOWARDS SYNTHETIC ENZYMES BASED ON PORPHYRINS AND STEROIDS [J].
BONARLAW, RP ;
MACKAY, LG ;
WALTER, CJ ;
MARVAUD, V ;
SANDERS, JKM .
PURE AND APPLIED CHEMISTRY, 1994, 66 (04) :803-810
[4]   Bioorganometallic chemistry .8. The molecular recognition of aromatic and aliphatic amino acids and substituted aromatic and aliphatic carboxylic acid guests with supramolecular (eta(5)-pentamethylcyclopentadienyl)rhodium-nucleobase, nucleoside, and nucleotide cyclic trimer hosts via non-covalent pi-pi and hydrophobic interactions in water: Steric, electronic, and conformational parameters [J].
Chen, H ;
Ogo, S ;
Fish, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :4993-5001
[5]  
CHEN H, 1995, J AM CHEM SOC, V117, P4993
[6]   ENANTIOSELECTIVE RECOGNITION OF HISTIDINE AND LYSINE ESTERS BY PORPHYRIN CHIRAL CLEFTS AND DETECTION OF AMINO-ACID CONFORMATIONS IN THE BOUND-STATE [J].
CROSSLEY, MJ ;
MACKAY, LG ;
TRY, AC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1925-1927
[7]   A RECEPTOR FOR THE ENANTIOSELECTIVE RECOGNITION OF PHENYLALANINE AND TRYPTOPHAN UNDER NEUTRAL CONDITIONS [J].
GALAN, A ;
ANDREU, D ;
ECHAVARREN, AM ;
PRADOS, P ;
DEMENDOZA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1511-1512
[8]  
HAMILTON AD, 1995, TETRAHEDRON S, V56, P51
[9]   MOLECULAR RECOGNITION VIA BASE-PAIRING - PHOTOINDUCED ELECTRON-TRANSFER IN HYDROGEN-BONDED ZINC PORPHYRIN BENZOQUINONE CONJUGATES [J].
HARRIMAN, A ;
KUBO, Y ;
SESSLER, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) :388-390
[10]   A NOVEL ANION-BINDING CHIRAL RECEPTOR-BASED ON A METALLOPORPHYRIN WITH MOLECULAR ASYMMETRY - HIGHLY ENANTIOSELECTIVE RECOGNITION OF AMINO-ACID DERIVATIVES [J].
KONISHI, K ;
YAHARA, K ;
TOSHISHIGE, H ;
AIDA, T ;
INOUE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1337-1344