BIOSYNTHESIS OF THE MARINE ANTIBIOTIC PENTABROMOPSEUDILIN .1. THE BENZENE-RING

被引：28

作者：

HANEFELD, U

FLOSS, HG

LAATSCH, H

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY

[2] UNIV WASHINGTON,DEPT CHEM,BG-10,SEATTLE,WA 98195

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 13期

关键词：

D O I：

10.1021/jo00092a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The biosynthesis of the potent marine antibiotic, pentabromopseudilin (1), was investigated in Alteromonas luteoviolaceus grown in a complex medium by feeding experiments with C-13-acetate, various amino acids, and differently labeled glucoses. The results show that the benzene ring of 1 originates from the shikimate pathway via p-hydroxybenzoic acid as a direct precursor. No incorporation of C-13 into the pyrrole ring was observed in any of these experiments.

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页码：3604 / 3608

页数：5

相关论文

共 12 条

[1] AUTOTOXIC ANTIBIOTIC PRODUCTION BY A MARINE CHROMOBACTERIUM [J].

ANDERSEN, RJ ;

WOLFE, MS ;

FAULKNER, DJ .

MARINE BIOLOGY, 1974, 27 (04) :281-285

[2] PRODUCTION OF A PYRROLE ANTIBIOTIC BY A MARINE BACTERIUM [J].

BURKHOLDER, PR ;

PFISTER, RM ;

LEITZ, FH .

APPLIED MICROBIOLOGY, 1966, 14 (04) :649-+

[3] THE BIOSYNTHESIS OF THE ANTIBIOTIC PYRROLNITRIN BY PSEUDOMONAS-AUREOFACIENS [J].

CHANG, CJ ;

FLOSS, HG ;

HOOK, DJ ;

MABE, JA ;

MANNI, PE ;

MARTIN, LL ;

SCHRODER, K ;

SHIEH, TL .

JOURNAL OF ANTIBIOTICS, 1981, 34 (05) :555-566

[4] VERRUCARINS AND RORIDINS .37. BIOSYNTHESIS OF THE ANTIBIOTIC VERRUCARIN-E - USE OF [1-C-13]-, [2-C-13], [1,2-C-13] AND [2-C-13,2-H-2(3)]-ACETATES [J].

CHEXAL, KK ;

SNIPES, C ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1980, 63 (04) :761-768

[5] SYNTHESIS OF A BROMINE-RICH MARINE ANTIBIOTIC [J].

HANESSIAN, S ;

KALTENBRONN, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (19) :4509-+

[6] STUDIES ON THE BIOSYNTHESIS OF VIOLACEIN .3. BIOSYNTHESIS OF VIOLACEIN - EVIDENCE FOR THE INTERMEDIACY OF 5-HYDROXY-L-TRYPTOPHAN AND THE STRUCTURE OF A NEW PIGMENT, OXYVIOLACEIN, PRODUCED BY THE METABOLISM OF 5-HYDROXYTRYPTOPHAN [J].

HOSHINO, T ;

OGASAWARA, N .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (09) :2339-2346

[7] SPECTROSCOPIC PROPERTIES OF VIOLACEIN AND RELATED-COMPOUNDS - CRYSTAL-STRUCTURE OF TETRAMETHYLVIOLACEIN [J].

LAATSCH, H ;

THOMSON, RH ;

COX, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (08) :1331-1339

[8]

LAATSCH H, 1989, LIEBIGS ANN CHEM, P863

[9]

LAATSCH H, UNPUB CHEM PHARM B

[10] STRUCTURE OF A BROMINE-RICH MARINE ANTIBIOTIC [J].

LOVELL, FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (19) :4510-&