An artificial aspartic proteinase system

被引:16
作者
Jiang, L
Liu, ZL
Liang, Z
Gao, YH
机构
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100101, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
关键词
crown ether derivatives; carboxyl; aspartic proteinases; artificial enzymes; nucleophilic catalytic mechanism;
D O I
10.1016/j.bmc.2005.03.026
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of aza crown ether derivatives with or without carboxyl groups in their side arms were synthesized and the former showed deacylation activities toward amino acid p-nitrophenyl ester hydrohalides. Substrate-selective phenomena were also observed. The relationship between the structures and deacylation activities of corresponding compounds suggested a nucleophilic catalytic mechanism. The results partially simulate some aspartic proteinases in the case of catalytic mechanism and are also useful for us to understand the detailed catalytic process of aspartic proteinases. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3673 / 3680
页数:8
相关论文
共 23 条
[2]   HOST-GUEST COMPLEXATION .21. CATALYSIS AND CHIRAL RECOGNITION THROUGH DESIGNED COMPLEXATION OF TRANSITION-STATES IN TRANSACYLATIONS OF AMINO ESTER SALTS [J].
CHAO, Y ;
WEISMAN, GR ;
SOGAH, GDY ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4948-4958
[3]  
CLEMENT GE, 1973, PROG BIOORG CHEM, V2, P177
[4]   CRYOENZYMOLOGY OF PORCINE PEPSIN [J].
DUNN, BM ;
FINK, AL .
BIOCHEMISTRY, 1984, 23 (22) :5241-5247
[5]  
HOFFMANN T, 1984, BIOCHEMISTRY-US, V23, P5247
[6]   PENICILLOPEPSIN FROM PENICILLIUM-JANTHINELLUM CRYSTAL-STRUCTURE AT 2.8-A AND SEQUENCE HOMOLOGY WITH PORCINE PEPSIN [J].
HSU, IN ;
DELBAERE, LTJ ;
JAMES, MNG .
NATURE, 1977, 266 (5598) :140-145
[7]   HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE .2. USE OF PH RATE STUDIES AND SOLVENT KINETIC ISOTOPE EFFECTS TO ELUCIDATE DETAILS OF CHEMICAL MECHANISM [J].
HYLAND, LJ ;
TOMASZEK, TA ;
MEEK, TD .
BIOCHEMISTRY, 1991, 30 (34) :8454-8463
[8]   HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE .1. INITIAL VELOCITY STUDIES AND KINETIC CHARACTERIZATION OF REACTION INTERMEDIATES BY O-18 ISOTOPE EXCHANGE [J].
HYLAND, LJ ;
TOMASZEK, TA ;
ROBERTS, GD ;
CARR, SA ;
MAGAARD, VW ;
BRYAN, HL ;
FAKHOURY, SA ;
MOORE, ML ;
MINNICH, MD ;
CULP, JS ;
DESJARLAIS, RL ;
MEEK, TD .
BIOCHEMISTRY, 1991, 30 (34) :8441-8453
[9]   FORMATION OF COMPLEXES BETWEEN AZA DERIVATIVES OF CROWN ETHERS AND PRIMARY ALKYLAMMONIUM SALTS .1. MONOAZA DERIVATIVES [J].
JOHNSON, MR ;
SUTHERLAND, IO ;
NEWTON, RF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (02) :357-371
[10]   Analogues of aspartic proteases synthesized by densely covering silica gel with carboxyl groups [J].
Kim, H ;
Chung, YS ;
Paik, H ;
Kim, MS ;
Suh, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (19) :2663-2666