BIOSYNTHESIS OF EPIDITHIODIOXOPIPERAZINES

被引：3

作者：

KIRBY, GW

机构：

[1] Department of Chemistry, University of Glasgow, Glasgow

来源：

PURE AND APPLIED CHEMISTRY | 1979年 / 51卷 / 04期

关键词：

D O I：

10.1351/pac197951040705

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Studies on the biosynthesis of gliotoxin (3), the first known member of the epidithiodioxopiperazine group of fungal metabolites, are reviewed. Phenylalanine is incorporated into gliotoxin, without loss or migration of aryl-hydrogen, by a pathway which may involve an arene oxide. cyclo-(L-Phenylalanyl-L-seryl) is identified as an intermediate and is efficiently (ca. 50%) converted into gliotoxin in Trichoderma viride. Structural analogues of cyclo-(L-Phe-L-Ser) are also efficiently metabolised and their products provide insight into the nature, and possibly sequence, of transformations occurring in the organism. © IUPAC

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页码：705 / 708

页数：4

相关论文

共 20 条

[1] BIOSYNTHETIC STUDIES .2. MODE OF INCORPORATION OF PHENYLALANINE INTO GLIOTOXIN [J].

BOSE, AK ;

KHANCHAN.KS ;

TAVARES, R ;

FUNKE, PT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (13) :3593-&

[2] BIOSYNTHETIC STUDIES ON GLIOTOXIN USING STABLE ISOTOPES AND MASS SPECTRAL METHODS [J].

BOSE, AK ;

DAS, KG ;

FUNKE, PT ;

KUGAJEVSKY, I ;

SHUKLA, OP ;

KHANCHANDANI, KS ;

SUHADOLNIK, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (04) :1038-+

[3] BIOSYNTHESIS OF DITHIADIKETOPIPERAZINE ANTIBIOTICS - COMPARISON OF POSSIBLE AROMATIC AMINO ACID PRECURSORS [J].

BRANNON, DR ;

MABE, JA ;

MOLLOY, BB ;

DAY, WA .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1971, 43 (03) :588-&

[4] BIOSYNTHESIS OF GLIOTOXIN [J].

BULOCK, JD ;

LEIGH, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (15) :628-629

[5]

BULOCK JD, 1970, CHEM COMMUN, P1404

[6]

BULOCK JD, COMMUNICATION

[7]

JOHNS N, UNPUBLISHED

[8]

JOHNS N, 1971, CHEM COMMUN, P163

[9] SYNTHESIS OF TRYPTOPHAN STEREOSELECTIVELY LABELED WITH TRITIUM AND DEUTERIUM IN BETA-METHYLENE GROUP - STERIC COURSE OF HYDROXYLATION IN SPORIDESMIN BIOSYNTHESIS [J].

KIRBY, GW ;

VARLEY, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (20) :833-834

[10] ANALOG BIOSYNTHESIS IN TRICHODERMA-VIRIDE - FORMATION OF 3A-DEOXYGLIOTOXIN [J].

KIRBY, GW ;

ROBINS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (10) :354-355