BIOSYNTHETIC ORIGIN OF [77]PARACYCLOPHANES FROM CYANOBACTERIA

被引:38
作者
BOBZIN, SC [1 ]
MOORE, RE [1 ]
机构
[1] UNIV HAWAII MANOA, DEPT CHEM, 2545 THE MALL, HONOLULU, HI 96822 USA
关键词
D O I
10.1016/S0040-4020(01)87237-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The biosyntheses of nostocyclophane D (1) and cylindrocyclophane D (2) have been investigated by the administration of sodium [1,2-C-13(2)]acetate, sodium [2-C-13,H-2(3)]acetate, sodium [2-C-13,H-2(3)]acetate, sodium [H-2(3)]acetate, sodium [1-C-13,O-18(2)]acetate, sodium [2-C-13,O-18(2)]acetate, L-[methyl-C-13]methionine, and L-[methyl-C-13,H-2(3)]methionine to cultures of the cyanobacteria Nostoc linckia and Cylindrospermum licheniforme, respectively. The isotopically labeled compounds produced by these feeding experiments indicate that the structural skeletons of these [7.7]paracyclophanes are polyketides that have been constructed by dimerization of acetate-derived nonaketides. Acetate has also been identified as the source of the branched methyl groups in cylindrocyclophane D.
引用
收藏
页码:7615 / 7626
页数:12
相关论文
共 39 条
[2]   BIOSYNTHESIS OF THE FUNGAL METABOLITES ALTERNARIOL, MELLEIN, RUBROFUSARIN, AND 6-METHYLSALICYLIC ACID FROM CD3CO2H [J].
ABELL, C ;
GARSON, MJ ;
LEEPER, FJ ;
STAUNTON, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (17) :1011-1013
[3]   BIOSYNTHESES OF ANTIBIOTIC A26771B BY PENICILLIUM-TURBATUM AND DEHYDROCURVULARIN BY ALTERNARIA-CINERARIAE - COMPARISON OF STEREOCHEMISTRY OF POLYKETIDE AND FATTY-ACID ENOYL THIOL ESTER REDUCTASES [J].
ARAI, K ;
RAWLINGS, BJ ;
YOSHIZAWA, Y ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3391-3399
[4]   BIOSYNTHESIS OF THE MACROTETROLIDE ANTIBIOTICS - THE INCORPORATION OF C-13 AND O-18 LABELED ACETATE, PROPIONATE, AND SUCCINATE [J].
ASHWORTH, DM ;
ROBINSON, JA ;
TURNER, DL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1719-1727
[5]   SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].
BAX, A ;
SUBRAMANIAN, S .
JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569
[6]   TOLYTOXIN AND NEW SCYTOPHYCINS FROM 3 SPECIES OF SCYTONEMA [J].
CARMELI, S ;
MOORE, RE ;
PATTERSON, GML .
JOURNAL OF NATURAL PRODUCTS, 1990, 53 (06) :1533-1542
[7]  
CARMELI S, 1991, J NAT PRODUCTS, V54, P1469
[8]   NAMING OF CYCLIC HEPTAPEPTIDE TOXINS OF CYANOBACTERIA (BLUE-GREEN-ALGAE) [J].
CARMICHAEL, WW ;
BEASLEY, V ;
BUNNER, DL ;
ELOFF, JN ;
FALCONER, I ;
GORHAM, P ;
HARADA, KI ;
KRISHNAMURTHY, T ;
YU, MJ ;
MOORE, RE ;
RINEHART, K ;
RUNNEGAR, M ;
SKULBERG, OM ;
WATANABE, M .
TOXICON, 1988, 26 (11) :971-973
[9]   STRUCTURES OF NOSTOCYCLOPHANES-A-D [J].
CHEN, JL ;
MOORE, RE ;
PATTERSON, GML .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4360-4364
[10]  
CHEN JL, 1991, THESIS U HAWAII