Biosynthesis of dictyopterene A:: stereoselectivity of a lipoxygenase/hydroperoxide lyase from Gomphonema parvulum (Bacillariophyceae)

被引：22

作者：

Hombeck, M ^{[1
]}

Pohnert, G ^{[1
]}

Boland, W ^{[1
]}

机构：

[1] Max Planck Inst Chem Ecol, D-07745 Jena, Germany

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 03期

关键词：

D O I：

10.1039/a808409b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(9S)-Hydroperoxyicosatetraenoic (9S-HPETE) acid is shown to be an intermediate in the biosynthesis of dictyopterene A in the freshwater diatom Gomphonema parvulum; the stereochemistry of (9S)-HPETE and the position of the hydrogen atom at C(16) lost during fatty acid cyclisation and oxidative cleavage of the hydroperoxide were investigated using trapping experiments and chirally deuterium labelled fatty acids.

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页码：243 / 244

页数：2

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共 10 条

[1] BIOSYNTHESIS OF ALGAL PHEROMONES - A MODEL STUDY WITH THE COMPOSITE SENECIO-ISATIDEUS [J].

BOLAND, W ;

MERTES, K .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1985, 147 (01) :83-91

[2] THE CHEMISTRY OF GAMETE ATTRACTION - CHEMICAL STRUCTURES, BIOSYNTHESIS, AND (A)BIOTIC DEGRADATION OF ALGAL PHEROMONES [J].

BOLAND, W .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (01) :37-43

[3] ESTERIFICATION OF N-PROTECTED ALPHA-AMINO-ACIDS WITH ALCOHOL/CARBODIIMIDE/4-(DIMETHYLAMINO)-PYRIDINE - RACEMIZATION OF ASPARTIC AND GLUTAMIC-ACID DERIVATIVES [J].

DHAON, MK ;

OLSEN, RK ;

RAMASAMY, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1962-1965

[4] BIOSYNTHESIS, STRUCTURE AND BIOLOGICAL-ACTIVITY OF HYDROXYEICOSATETRAENOIC ACIDS IN HYDRA-VULGARIS [J].

DIMARZO, V ;

DEPETROCELLIS, L ;

GIANFRANI, C ;

CIMINO, G .

BIOCHEMICAL JOURNAL, 1993, 295 :23-29

[5] BIOSYNTHESIS OF VICINAL DIHYDROXY FATTY-ACIDS IN THE RED ALGA GRACILARIOPSIS-LEMANEIFORMIS - IDENTIFICATION OF A SODIUM-DEPENDENT 12-LIPOXYGENASE AND A HYDROPEROXIDE ISOMERASE [J].

HAMBERG, M ;

GERWICK, WH .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1993, 305 (01) :115-122

[6] Biosynthesis of the algal pheromone fucoserratene by the freshwater diatom Asterionella formosa (Bacillariophyceae) [J].

Hombeck, M ;

Boland, W .

TETRAHEDRON, 1998, 54 (37) :11033-11042

[7] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[8] Biosynthesis of the algal pheromone hormosirene by the freshwater diatom Gomphonema parvulum (Bacillariophyceae) [J].

Pohnert, G ;

Boland, W .

TETRAHEDRON, 1996, 52 (30) :10073-10082

[9] PHEROMONES OF MARINE BROWN-ALGAE - A NEW BRANCH OF THE EICOSANOID METABOLISM [J].

STRATMANN, K ;

BOLAND, W ;

MULLER, DG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (09) :1246-1248

[10] Lipoxygenase-mediated formation of hydrocarbons and unsaturated aldehydes in freshwater diatoms [J].

Wendel, T ;

Juttner, F .

PHYTOCHEMISTRY, 1996, 41 (06) :1445-1449