BIOSYNTHESIS OF AXENOMYCIN-D - INCORPORATION OF C-13-LABELED PRECURSORS INTO THE MENADIONE CHROMOPHORE, DEOXYSUGARS AND THE AXENOLIDE

被引:8
作者
FRIESE, V
BOOS, A
BAUCH, HJ
LEISTNER, E
机构
[1] UNIV BONN,INST PHARMAZEUT BIOL,W-5300 BONN,GERMANY
[2] ST JOHANNES HOSP,ZENT LAB,W-4600 DORTMUND,GERMANY
关键词
STREPTOMYCES-LISANDRI; AXENOMYCIN; MENADIONE; BIOSYNTHESIS; C-13 NMR SPECTROSCOPY;
D O I
10.1016/S0031-9422(00)95145-8
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
Experiments on the biosynthesis of the menadione chromophore of axenomycin D in Streptomyces lisandri resulted in the specific incorporation of label from L-[C-13-Me]methionine, [1-C-13]propionate, [2,3-C-13(2)]propionate, [3-C-13]propionate, [U-C-13(3)]glycerol and [U-C-13(6)]glucose. The data indicate that the menadione chromophore is derived from a metabolite of the shikimate pathway. The mode of incorporation shows, however, that the biosynthesis of the menadione chromophore of axenomycins differs from the biosynthesis of the menadione chromophore of menaquinones.
引用
收藏
页码:613 / 621
页数:9
相关论文
共 13 条
[1]   AXENOMYCINS .2. STRUCTURE OF AXENOLIDE [J].
ARCAMONE, F ;
FRANCESCHI, G ;
GIOIA, B ;
PENCO, S ;
VIGEVANI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (06) :2009-2011
[2]   AXENOMYCINS .1. STRUCTURE OF CHROMOPHORE AND SUGAR MOIETIES [J].
ARCAMONE, F ;
BARBIERI, W ;
FRANCESCHI, G ;
PENCO, S ;
VIGEVANI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (06) :2008-2009
[3]  
BAUCH HJ, 1980, Z NATURFORSCH C, V35, P936
[4]  
BENTLEY R, 1987, CELLULAR MOL BIOL, P512
[5]   AXENOMYCINS, NEW ANTHELMINTIC, ANTIPROTOZOAL AND ANTIFUNGAL ANTIBIOTICS, PRODUCED BY STREPTOMYCES-LISANDRI NOV-SP [J].
BIANCHI, M ;
COTTA, E ;
FERNI, G ;
GREIN, A ;
JULITA, P ;
MAZZOLENI, R ;
SPALLA, C .
ARCHIVES OF MICROBIOLOGY, 1974, 98 (04) :289-299
[6]   STUDIES ON THE BIOSYNTHESIS OF THE ALPHA-GLUCOSIDASE INHIBITOR ACARBOSE - VALIENAMINE, A M-C7N UNIT NOT DERIVED FROM THE SHIKIMATE PATHWAY [J].
DEGWERT, U ;
VANHULST, R ;
PAPE, H ;
HERROLD, RE ;
BEALE, JM ;
KELLER, PJ ;
LEE, JP ;
FLOSS, HG .
JOURNAL OF ANTIBIOTICS, 1987, 40 (06) :855-861
[7]   AXENOMYCINS, NEW CESTOCIDAL ANTIBIOTICS [J].
DELLABRUNA, C ;
RICCIARDI, ML ;
SANFILIPPO, A .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1973, 3 (06) :708-710
[8]   STUDIES ON THE BIOSYNTHESIS OF ANTIBIOTICS [J].
FLOSS, HG ;
KELLER, PJ ;
BEALE, JM .
JOURNAL OF NATURAL PRODUCTS, 1986, 49 (06) :957-970
[9]   Synthesis of alkylphenanthrenes Part III 1 2 7-, 1 3 7-, and 1 6 7-trimethylphenanthrenes [J].
Haworth, RD ;
Bolam, FM .
JOURNAL OF THE CHEMICAL SOCIETY, 1932, :2248-2251
[10]   SUBCELLULAR COMPARTMENTATION OF SHIKIMIC ACID AND PHENYLALANINE IN BUCKWHEAT CELL-SUSPENSION CULTURES GROWN IN THE PRESENCE OF SHIKIMATE PATHWAY INHIBITORS [J].
HOLLANDERCZYTKO, H ;
AMRHEIN, N .
PLANT SCIENCE LETTERS, 1983, 29 (01) :89-96