Assignment of absolute configuration of the alpha,beta-unsaturated gamma-methyl-gamma-lactone of the annonaceous acetogenins by a simple enzymatic method

被引:18
作者
Duret, P
Waechter, AI
Figadere, B
Hocquemiller, R
Cave, A
Pierard, C
Peres, M
机构
[1] UNIV PARIS SUD,FAC PHARM,CNRS,LAB PHARMACOGNOISE,F-92296 CHATENAY MALABRY,FRANCE
[2] INST MED AEROSPATIALE,DEPT NEUROPHYSIOL AEROSPATIALE,LAB RMN,F-91223 BRETIGNY SUR ORGE,FRANCE
关键词
D O I
10.1016/0040-4039(96)01592-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute configuration of the C-36 or C-34 chiral centers of Annonaceous acetogenins has been determined by simple enzymatic method focusing on the HPLC detection of NADH issued from the enzymatic oxidation of L- or D-lactic acid (obtained by oxidative cleavage of the terminal alpha,beta-unsaturated gamma-methyl-gamma-lactone) to pyruvic acid by lactate dehydrogenase. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:7043 / 7046
页数:4
相关论文
共 12 条
[1]  
CAVE A, 1996, PROGR CHEM ORGANIC N
[2]  
Gutmann I., 1974, Methods of Enzymatic Analysis, P1464
[3]   DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ANNONIN-I, A BIOACTIVE NATURAL ACETOGENIN FROM ANNONA-SQUAMOSA [J].
GYPSER, A ;
BULOW, C ;
SCHARF, HD .
TETRAHEDRON, 1995, 51 (07) :1921-1930
[4]   ENANTIOSPECIFIC PREPARATION OF THE LACTONE FRAGMENT OF MURISOLIN .8. [J].
HARMANGE, JC ;
FIGADERE, B ;
HOCQUEMILLER, R .
TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :347-350
[5]   STEREOSTRUCTURAL STUDIES ON THE 4-HYDROXYLATED ANNONACEOUS ACETOGENINS - A NOVEL USE OF MOSHER ESTER DATA FOR DETERMINING RELATIVE CONFIGURATION [BETWEEN C(4) AND C(36)] [J].
HOYE, TR ;
HANSON, PR ;
HASENWINKEL, LE ;
RAMIREZ, EA ;
ZHUANG, ZP .
TETRAHEDRON LETTERS, 1994, 35 (46) :8529-8532
[6]   DESACETYLUVARICIN FROM UVARIA-ACCUMINATA, CONFIGURATION OF UVARICIN AT C-36 [J].
JOLAD, SD ;
HOFFMANN, JJ ;
COLE, JR ;
BARRY, CE ;
BATES, RB ;
LINZ, GS ;
KONIG, WA .
JOURNAL OF NATURAL PRODUCTS, 1985, 48 (04) :644-645
[7]  
RAMIREZ EA, 1995, STUDIES NATURAL PROD, P251
[8]   DETERMINATION OF ABSOLUTE-CONFIGURATION OF STEREOGENIC CARBINOL CENTERS IN ANNONACEOUS ACETOGENINS BY H-1-NMR AND F-19-NMR ANALYSIS OF MOSHER ESTER DERIVATIVES [J].
RIESER, MJ ;
HUI, YH ;
RUPPRECHT, JK ;
KOZLOWSKI, JF ;
WOOD, KV ;
MCLAUGHLIN, JL ;
HANSON, PR ;
ZHUANG, ZP ;
HOYE, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10203-10213
[9]   FURTHER BUTENOLIDES FROM THE CARIBBEAN OCTOCORAL PTEROGORGIA-CITRINA [J].
RODRIGUEZ, AD ;
RAMIREZ, C .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (03) :339-347
[10]   ANNONACEOUS ACETOGENINS - A REVIEW [J].
RUPPRECHT, JK ;
HUI, YH ;
MCLAUGHLIN, JL .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (02) :237-278