MICROBIAL OXIDATION OF THE ANTIMALARIAL DRUG ARTEETHER

被引:21
作者
HU, YL [1 ]
ZIFFER, H [1 ]
LI, GY [1 ]
YEH, HJC [1 ]
机构
[1] NIDDK,ANALYT CHEM LAB,BETHESDA,MD 20892
关键词
D O I
10.1016/0045-2068(92)90035-2
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
Three oxidation products from the action of the enzymes in Beauveria sulfurescens on the antimalarial drug arteether were isolated and their structures established by mass spectrometry, and both 1D and 2D NMR. Two of the compounds, 14-hydroxyarteether and 9β-hydroxyarteether retained the peroxide bridge required for biological activity. The metabolites were employed as intermediates for the preparation of other products. © 1992.
引用
收藏
页码:148 / 154
页数:7
相关论文
共 15 条
[1]   MICROBIAL TRANSFORMATIONS .8. 1ST EXAMPLE OF A HIGHLY ENANTIOSELECTIVE MICROBIOLOGICAL HYDROXYLATION PROCESS [J].
ARCHELAS, A ;
FOURNERON, JD ;
FURSTOSS, R ;
CESARIO, M ;
PASCARD, C .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1797-1799
[2]  
BAKER JK, 1988, BIOMED ENVIRON MASS, V18, P337
[3]   MICROBIAL TRANSFORMATIONS .10. EVIDENCE FOR A CARBON-RADICAL INTERMEDIATE IN THE BIOHYDROXYLATIONS ACHIEVED BY THE FUNGUS BEAUVERIA-SULFURESCENS [J].
FOURNERON, JD ;
ARCHELAS, A ;
FURSTOSS, R .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2478-2483
[4]  
FOURNERON JD, 1987, TETRAHEDRON, V47, P2273
[5]   PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].
GRIFFITH, WP ;
LEY, SV ;
WHITCOMBE, GP ;
WHITE, AD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627
[6]  
HU Y, 1992, J LABELLED COMPD RAD, V29, P1293
[7]   MICROBIAL HYDROXYLATION OF A DIHYDROARTEMISININ DERIVATIVE [J].
HU, YL ;
HIGHET, RJ ;
MARION, D ;
ZIFFER, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1176-1177
[8]   H-1 AND C-13 NMR ASSIGNMENTS OF ARTEETHERS [J].
HUFFORD, CD ;
ELSOHLY, HN .
SPECTROSCOPY LETTERS, 1987, 20 (05) :439-444
[9]   NUCLEOPHILIC BOROHYDRIDE - SELECTIVE REDUCTIVE DISPLACEMENT OF HALIDES, SULFONATE ESTERS, TERTIARY-AMINES, AND N,N-DISULFONIMIDES WITH BOROHYDRIDE REAGENTS IN POLAR APROTIC-SOLVENTS [J].
HUTCHINS, RO ;
KANDASAMY, D ;
DUX, F ;
MARYANOFF, CA ;
ROTSTEIN, D ;
GOLDSMITH, B ;
BURGOYNE, W ;
CISTONE, F ;
DALESSANDRO, J ;
PUGLIS, J .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2259-2268
[10]  
JOHNSON RA, 1978, OXIDATION ORGANIC C, P131