STEREOSELECTIVE FORMATION OF BENZ[A]ANTHRACENE (+)-(5S,6R)-OXIDE AND (+)-(8R,9S)-OXIDE BY A HIGHLY PURIFIED AND RECONSTITUTED SYSTEM CONTAINING CYTOCHROME P-450C

被引:49
作者
VANBLADEREN, PJ
ARMSTRONG, RN
COBB, D
THAKKER, DR
RYAN, DE
THOMAS, PE
SHARMA, ND
BOYD, DR
LEVIN, W
JERINA, DM
机构
[1] UNIV MARYLAND,DEPT CHEM,COLLEGE PK,MD 20034
[2] QUEENS UNIV BELFAST,DEPT CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND
[3] HOFFMANN LA ROCHE INC,DEPT BIOCHEM & DRUG METAB,NUTLEY,NJ 07110
关键词
D O I
10.1016/0006-291X(82)91153-6
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
引用
收藏
页码:602 / 609
页数:8
相关论文
共 26 条
[1]   ANTHRACENE 1,2-OXIDE - SYNTHESIS AND ROLE IN THE METABOLISM OF ANTHRACENE BY MAMMALS [J].
AKHTAR, MN ;
HAMILTON, JG ;
BOYD, DR ;
BRAUNSTEIN, A ;
SEIFRIED, HE ;
JERINA, DM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1442-1446
[2]   STEREOSELECTIVITY OF RAT-LIVER CYTOCHROME P-450C ON FORMATION OF BENZO[A]PYRENE 4,5-OXIDE [J].
ARMSTRON, RN ;
LEVIN, W ;
RYAN, DE ;
THOMAS, PE ;
MAH, HD ;
JERINA, DM .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1981, 100 (03) :1077-1084
[3]  
ARMSTRONG RN, 1981, J BIOL CHEM, V256, P4726
[4]   REACTIONS OF K-REGION OXIDES OF CARCINOGENIC AND RELATED POLYCYCLIC-HYDROCARBONS WITH NUCLEOPHILES - STEREOCHEMISTRY AND REGIOSELECTIVITY [J].
BELAND, FA ;
HARVEY, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (16) :4963-4970
[5]   SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF (+)-BENZ[A]ANTHRACENE AND (-)-BENZ[A]ANTHRACENE 8,9-OXIDE AND DERIVED MAMMALIAN LIVER METABOLITES OF BENZ[A]-ANTHRACENE [J].
BOYD, DR ;
DAWSON, KA ;
GADAGINAMATH, GS ;
HAMILTON, JG ;
MALONE, JF ;
SHARMA, ND .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01) :94-97
[6]   TUMORIGENICITY OF OPTICAL ENANTIOMERS OF DIASTEREOMERIC BENZO[A]PYRENE 7,8-DIOL-9,10-EPOXIDES IN NEWBORN MICE - EXCEPTIONAL ACTIVITY OF(+)-7-BETA, 8-ALPHA-DIHYDROXY-9-ALPHA, 10-ALPHA-EPOXY-7,8.9.10-TETRAHYDROBENZOL[A]PYRENE [J].
BUENING, MK ;
WISLOCKI, PG ;
LEVIN, W ;
YAGI, H ;
THAKKER, DR ;
AKAGI, H ;
KOREEDA, M ;
JERINA, DM ;
CONNEY, AH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1978, 75 (11) :5358-5361
[7]   DIFFERENCES IN MUTAGENICITY AND CYTOTOXICITY OF (+)-BENZO[ALPHA]PYRENE AND (-)-BENZO[ALPHA]PYRENE 4,5-OXIDE - SYNERGISTIC INTERACTION OF ENANTIOMERS [J].
CHANG, RL ;
WOOD, AW ;
LEVIN, W ;
MAH, HD ;
THAKKER, DR ;
JERINA, DM ;
CONNEY, AH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (09) :4280-4284
[8]   REGIOSPECIFICITY AND STEREOSPECIFICITY IN THE ENZYMATIC CONJUGATION OF GLUTATHIONE WITH +/-BENZO(A)PYRENE 4,5-OXIDE [J].
HERNANDEZ, O ;
WALKER, M ;
COX, RH ;
FOUREMAN, GL ;
SMITH, BR ;
BEND, JR .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1980, 96 (04) :1494-1502
[9]   C-13 NUCLEAR MAGNETIC-RESONANCE STUDY OF NUCLEOPHILIC ADDITIONS TO BENZO[A]PYRENE 4,5-OXIDE AND OF ITS ACID-CATALYZED REARRANGEMENT [J].
HYLARIDES, MD ;
LYLE, TA ;
DAUB, GH ;
VANDERJAGT, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4652-4657
[10]   NOVEL REARRANGEMENTS DURING DEHYDRATION OF NUCLEOPHILE ADDUCTS OF ARENE OXIDES - REAPPRAISAL OF PRE-MERCAPTURIC ACID STRUCTURES [J].
JEFFERY, AM ;
JERINA, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (15) :4427-4428