FAST AMIDE CLEAVAGE UNDER MILD CONDITIONS - AN EVOLUTIONARY APPROACH TO BIOORGANIC CATALYSIS

被引:21
作者
MENGER, FM
FEI, ZX
机构
[1] Department of Chemistry, Emory University, Atlanta, Georgia
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 03期
关键词
D O I
10.1002/anie.199403461
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The noncovalent aggregation of hexadecanoate in aqueous phosphate buffer with 3% acetonitrile gives rise to “catalytic clumps” that catalyze the hydrolysis of the amide group in 1. Amide cleavage is achieved with 108‐fold acceleration with catalyst concentrations of 10−5M at pH 7–8. These extremely simple catalysts, whose activity equals or exceeds that of catalytic antibodies, were found by rapid screening of hundreds of organic “clumps”. (Formula Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:346 / 348
页数:3
相关论文
共 21 条
[2]  
BLAGOEVA IB, 1985, J CHEM SOC PERK T 2, P1017, DOI 10.1039/p29850001017
[3]  
Eck J. C., 1943, ORG SYNTH, V2, P374
[4]   BILAYER-FORMING ION-PAIR AMPHIPHILES FROM SINGLE-CHAIN SURFACTANTS [J].
FUKUDA, H ;
KAWATA, K ;
OKUDA, H ;
REGEN, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (04) :1635-1637
[5]   NONPOLAR CONTRIBUTIONS TO RATE OF NUCLEOPHILIC DISPLACEMENTS OF P-NITROPHENYL ESTERS IN MICELLES [J].
GITLER, C ;
OCHOASOL.A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (18) :5004-&
[6]   RAPID AMIDE HYDROLYSIS MEDIATED BY COPPER AND ZINC [J].
GROVES, JT ;
DIAS, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :1033-1035
[7]   SOME COLLOIDAL PROPERTIES OF DECYL-AND DODECYLTRIMETHYLAMMONIUM DODECYL SULFATE [J].
HOYER, HW ;
ZOELLNER, M ;
MARMO, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1961, 65 (10) :1804-&
[8]   INDUCTION OF AN ANTIBODY THAT CATALYZES THE HYDROLYSIS OF AN AMIDE BOND [J].
JANDA, KD ;
SCHLOEDER, D ;
BENKOVIC, SJ ;
LERNER, RA .
SCIENCE, 1988, 241 (4870) :1188-1191
[9]   SPONTANEOUS VESICLE FORMATION IN AQUEOUS MIXTURES OF SINGLE-TAILED SURFACTANTS [J].
KALER, EW ;
MURTHY, AK ;
RODRIGUEZ, BE ;
ZASADZINSKI, JAN .
SCIENCE, 1989, 245 (4924) :1371-1374
[10]   INTRAMOLECULAR CATALYSIS OF AMIDE HYDROLYSIS BY 2 CARBOXY-GROUPS [J].
KIRBY, AJ ;
MCDONALD, RS ;
SMITH, CR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (12) :1495-1504