Kinamycin biosynthesis. Synthesis, isolation, and incorporation of stealthin C, an aminobenzo[b]fluorene

被引:92
作者
Gould, SJ
Melville, CR
Cone, MC
Chen, J
Carney, JR
机构
[1] Department of Chemistry, Oregon State University, Corvallis
关键词
D O I
10.1021/jo961486y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new intermediate in the biosynthesis of the benzo[b]fluorene antibiotic, kinamycin D, has been identified. 11-Amino-4,5,9-trihydroxy-2-methyl-10H-benzo[b]fluoren-10-one was synthesized and shown to be present in extracts of treptomyces murayamaensis fermentations. A deuterated sample was prepared and shown to be specifically incorporated into kinamycin D. This new intermediate, now named stealthin C, is also the probable hydroxylation substrate for the biosynthesis of stealthin A by S. Viridochromogenes.
引用
收藏
页码:320 / 324
页数:5
相关论文
共 31 条
[1]   CYSFLUORETIN, A NEW INHIBITOR OF GLUTATHIONE-S-TRANSFERASE, PRODUCED BY STREPTOMYCES SP MI384-DF12 [J].
AOYAMA, T ;
ZHAO, WJ ;
KOJIMA, F ;
MURAOKA, Y ;
NAGANAWA, H ;
TAKEUCHI, T ;
AOYAGI, T .
JOURNAL OF ANTIBIOTICS, 1993, 46 (09) :1471-1474
[2]   JADOMYCIN, A NOVEL 8H-BENZ[B]OXAZOLO[3,2-F]PHENANTHRIDINE ANTIBIOTIC FROM STREPTOMYCES-VENEZUELAE ISP5230 [J].
AYER, SW ;
MCINNES, AG ;
THIBAULT, P ;
WALTER, JA ;
DOULL, JL ;
PARNELL, T ;
VINING, LC .
TETRAHEDRON LETTERS, 1991, 32 (44) :6301-6304
[3]   NEW PRODUCTS RELATED TO KINAMYCIN FROM STREPTOMYCES-MURAYAMAENSIS .1. TAXONOMY, PRODUCTION, ISOLATION AND BIOLOGICAL PROPERTIES [J].
CONE, MC ;
SEATON, PJ ;
HALLEY, KA ;
GOULD, SJ .
JOURNAL OF ANTIBIOTICS, 1989, 42 (02) :179-188
[4]   KINAFLUORENONE, A BENZO[B]FLUORENONE ISOLATED FROM THE KINAMYCIN PRODUCER STREPTOMYCES-MURAYAMAENSIS [J].
CONE, MC ;
MELVILLE, CR ;
GORE, MP ;
GOULD, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1058-1061
[5]   DETECTION OF PHENANTHROVIRIDIN AGLYCONE IN A UV-MUTANT OF STREPTOMYCES-MURAYAMAENSIS [J].
CONE, MC ;
HASSAN, AM ;
GORE, MP ;
GOULD, SJ ;
BORDERS, DB ;
ALLURI, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1923-1924
[6]   SYNTHESIS OF PUTATIVE INTERMEDIATES IN THE BIOSYNTHESIS OF THE KINAMYCIN ANTIBIOTICS - TOTAL SYNTHESIS OF PHENANTHROVIRIDIN AGLYCON AND RELATED-COMPOUNDS [J].
GORE, MP ;
GOULD, SJ ;
WELLER, DD .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2774-2783
[7]   TOTAL SYNTHESIS OF PHENANTHROVIRIDIN AGLYCON - THE 1ST NATURALLY-OCCURRING BENZO[B]PHENANTHRIDINE [J].
GORE, MP ;
GOULD, SJ ;
WELLER, DD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2289-2291
[8]  
GOULD S, UNPUB
[9]   Identification of prekinamycin in extracts of Streptomyces murayamaensis [J].
Gould, SJ ;
Chen, J ;
Cone, MC ;
Gore, MP ;
Melville, CR ;
Tamayo, N .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5720-5721
[10]   REVISED STRUCTURES FOR THE KINAMYCIN ANTIBIOTICS - 5-DIAZOBENZO[B]FLUORENES RATHER THAN BENZO[B]CARBAZOLE CYANAMIDES [J].
GOULD, SJ ;
TAMAYO, N ;
MELVILLE, CR ;
CONE, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2207-2208