Unusual alkylation reactions in the biosynthesis of natural products and elucidation of their reaction mechanisms

被引:0
作者
Glasenapp-Breiling, M [1 ]
Montforts, FP [1 ]
机构
[1] Univ Bremen, Inst Organ Chem, FB Biol Chem 2, D-28334 Bremen, Germany
关键词
biosynthesis; cobalamins; methylations; radicals; radical reactions;
D O I
10.1002/(SICI)1521-3773(20000218)39:4<721::AID-ANIE721>3.0.CO;2-Y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Methylcorrinoids as methylation coenzymes in radical C-methylations: Unusual alkylation reactions at nonactivated carbon atoms of natural products can be explained for the first time by a unique reaction of methylcobalamin (1). According to the mechanistic course of the reaction the corrin part of the vitamin B12 derivative 1 undergoes substitution at the methyl group by carbon radicals with inversion of configuration.
引用
收藏
页码:721 / +
页数:4
相关论文
共 22 条
[1]  
ARIGONI D, 1969, TOPICS STEREOCHEMIST, V4
[2]  
DRENNAN CL, 1998, VITAMIN B12 B12 PROT, P133
[3]  
Floss H G, 1979, Adv Enzymol Relat Areas Mol Biol, V50, P243
[4]  
Galliker P., 1998, Vitamin B, V12, P447
[5]  
Golding B. T, 1998, VITAMIN B12 B12 PROT, P201
[6]  
Gordon A.J., 1972, CHEM COMPANION
[7]   STEREOCHEMISTRY OF METHYLATION IN THIENAMYCIN BIOSYNTHESIS - EXAMPLE OF A METHYL TRANSFER FROM METHIONINE WITH RETENTION OF CONFIGURATION [J].
HOUCK, DR ;
KOBAYASHI, K ;
WILLIAMSON, JM ;
FLOSS, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5365-5366
[8]  
KELLENBERGER L, 1996, CHIMIA, V50, P344
[9]   THERMODYNAMIC TRANS-EFFECTS OF THE NUCLEOTIDE BASE IN THE B-12 COENZYMES [J].
KRAUTLER, B .
HELVETICA CHIMICA ACTA, 1987, 70 (05) :1268-1278
[10]   OLIGOMETHYLENE-BRIDGED VITAMIN-B-12 DIMERS [J].
KRAUTLER, B ;
DERER, T ;
LIU, PL ;
MUHLECKER, W ;
PUCHBERGER, M ;
KRATKY, C ;
GRUBER, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (01) :84-86