A stereoselective fluorogenic assay for aldolases:: Detection of an anti-selective aldolase catalytic antibody

被引:37
作者
Jourdain, N [1 ]
Carlón, RP [1 ]
Reymond, JL [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland
关键词
D O I
10.1016/S0040-4039(98)02139-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoisomeric aldols 6a-d undergo retroaldolization to give 3-oxopropyl umbelliferyl ether 5 and subsequently umbelliferone 4 by beta-elimination, leading to a fluorescence increase at lambda(em) = 460 +/- 20 nm (lambda(ex) = 360 +/- 20 nm). This fluorogenic assay for aldolases operates in cell culture media and can be used to search for new stereoselective aldolase biocatalysts. Aldolase antibody 38C2 (Aldrich no. 47,995-0) catalyzes stereoselectively the retroaldolization of(S)-anti aldol 6c. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9415 / 9418
页数:4
相关论文
共 21 条
[1]   Immune versus natural selection: Antibody aldolases with enzymic rates but broader scope [J].
Barbas, CF ;
Heine, A ;
Zhong, GF ;
Hoffmann, T ;
Gramatikova, S ;
Bjornestedt, R ;
List, B ;
Anderson, J ;
Stura, EA ;
Wilson, IA ;
Lerner, RA .
SCIENCE, 1997, 278 (5346) :2085-2092
[2]  
ENDERS D, 1988, ANGEW CHEM, V100, P594
[3]   General strategies toward the syntheses of macrolide antibiotics. The total syntheses of 6-deoxyerythronolide B and oleandolide [J].
Evans, DA ;
Kim, AS ;
Metternich, R ;
Novack, VJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :5921-5942
[4]   BASE-CATALYZED BETA-ELIMINATION REACTIONS IN AQUEOUS SOLUTION .5. ELIMINATION FROM 4-PARA SUBSTITUTED-PHENOXY)-2-BUTANONES [J].
FEDOR, LR ;
GLAVE, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (04) :985-&
[5]  
Fessner WD, 1997, TOP CURR CHEM, V184, P97
[6]  
Groger H, 1998, CHEM-EUR J, V4, P1137
[7]   ACYCLIC STEREOSELECTION .4. ASSIGNMENT OF STEREOSTRUCTURE TO BETA-HYDROXYCARBONYL COMPOUNDS BY C-13 NUCLEAR MAGNETIC-RESONANCE [J].
HEATHCOCK, CH ;
PIRRUNG, MC ;
SOHN, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4294-4299
[8]   Aldolase antibodies of remarkable scope [J].
Hoffmann, T ;
Zhong, GF ;
List, B ;
Shabat, D ;
Anderson, J ;
Gramatikova, S ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2768-2779
[9]   Off-the-shelf proteins that rival tailor-made antibodies as catalysts [J].
Hollfelder, F ;
Kirby, AJ ;
Tawfik, DS .
NATURE, 1996, 383 (6595) :60-63
[10]   Albumin-catalyzed proton transfer [J].
Kikuchi, K ;
Thorn, SN ;
Hilvert, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8184-8185