BIOSYNTHETIC ORIGINS OF THE POLYCYCLIC XANTHONE ANTIBIOTIC, CITREAMICIN

被引:12
作者
CARTER, GT
BORDERS, DB
GOODMAN, JJ
ASHCROFT, J
GREENSTEIN, M
MAIESE, WM
PEARCE, CJ
机构
[1] Medical Research Division, American Cyanamid Company, Lederle Laboratories, Pearl River
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 09期
关键词
D O I
10.1039/p19910002215
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The biosynthesis of citreamicin 1 has been studied by feeding C-13- and O-18-labelled precursors to Micromonospora citrea cultures. C-13-NMR spectroscopic analysis of the enriched products demonstrated a labelling pattern indicating that the antibiotic is derived from a polyketide which undergoes rearrangement by a mechanism unique for xanthone biosynthesis.
引用
收藏
页码:2215 / 2219
页数:5
相关论文
共 22 条
[1]  
ATKINSON JE, 1968, J CHEM SOC CHEM COMM, P1386
[2]   THE FATE OF VALINE-OXYGEN DURING PENICILLIN BIOSYNTHESIS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BIRD, JW ;
SCHOFIELD, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (21) :1615-1616
[3]   BIOSYNTHESIS OF TAJIXANTHONE AND SHAMIXANTHONE BY ASPERGILLUS VARIECOLOR - INCORPORATION OF O-18 GAS [J].
BARDSHIRI, E ;
MCINTYRE, CR ;
SIMPSON, TJ ;
MOORE, RN ;
TRIMBLE, LA ;
VEDERAS, JC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (21) :1404-1406
[4]   AN NMR TECHNIQUE FOR TRACING OUT THE CARBON SKELETON OF AN ORGANIC-MOLECULE [J].
BAX, A ;
FREEMAN, R ;
FRENKIEL, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2102-2104
[5]   NATURAL ABUNDANCE C-13-C-13 COUPLING OBSERVED VIA DOUBLE-QUANTUM COHERENCE [J].
BAX, A ;
FREEMAN, R ;
KEMPSELL, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (14) :4849-4851
[6]  
BAX A, 1981, J MAGN RESON, V43, P4708
[7]   BIOSYNTHESIS OF MANGOSTIN .1. THE ORIGIN OF THE XANTHONE SKELETON [J].
BENNETT, GJ ;
LEE, HH ;
DAS, NP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10) :2671-2676
[8]   THE BIOSYNTHESIS OF MANGOSTIN - THE ORIGIN OF THE XANTHONE SKELETON [J].
BENNETT, GJ ;
LEE, HH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (09) :619-620
[9]   BIOSYNTHETIC ORIGIN OF THE CARBON SKELETON OF SIMAOMICIN-ALPHA, A HEXACYCLIC XANTHONE ANTIBIOTIC [J].
CARTER, GT ;
GOODMAN, JJ ;
TORREY, MJ ;
BORDERS, DB ;
GOULD, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) :4321-4323
[10]   CITREAMICINS, NOVEL ANTIBIOTICS FROM MICROMONOSPORA-CITREA - ISOLATION, CHARACTERIZATION, AND STRUCTURE DETERMINATION [J].
CARTER, GT ;
NIETSCHE, JA ;
WILLIAMS, DR ;
BORDERS, DB .
JOURNAL OF ANTIBIOTICS, 1990, 43 (05) :504-512