BIOSYNTHESIS OF ALGAE PHEROMONES .4. PERICYCLIC-REACTIONS IN NATURE - SPONTANEOUS COPE REARRANGEMENT INACTIVATES ALGAE PHEROMONES

被引：22

作者：

BOLAND, W ^{[1
]}

POHNERT, G ^{[1
]}

MAIER, I ^{[1
]}

机构：

[1] UNIV KONSTANZ,FAK BIOL,W-7750 CONSTANCE,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 15期

关键词：

BIOSYNTHESES; COPE REARRANGEMENTS; PERICYCLIC REACTIONS; PHEROMONES;

D O I：

10.1002/anie.199516021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A pheromone roughly 100 times more effective than cyclohepta‐1,4‐diene 2 (R = C2H5, ectocarpene) is its biosynthetic precursor 1. This thermally labile cis‐disubstituted cyclopropane is the actual signaling agent of the marine brown algae Ectocarpus siliculosus. The [3,3]sigmatropic rearrangement of 1 giving 2 (t1/2 = 21 min at 18°C) is the fastest known reaction for the spontaneous inactivation of a pheromone. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：1602 / 1604

页数：3

相关论文

共 23 条

[11] DICTYOTA-DICHOTOMA (PHAEOPHYCEAE) - IDENTIFICATION OF THE SPERM ATTRACTANT [J].

MULLER, DG ;

GASSMANN, G ;

BOLAND, W ;

MARNER, F ;

JAENICKE, L .

SCIENCE, 1981, 212 (4498) :1040-1041

[12] IDENTIFICATION OF A SEXUAL HORMONE AND RELATED SUBSTANCES IN THE MARINE BROWN ALGA DESMARESTIA [J].

MULLER, DG ;

PETERS, A ;

GASSMANN, G ;

BOLAND, W ;

MARNER, FJ ;

JAENICKE, L .

NATURWISSENSCHAFTEN, 1982, 69 (06) :290-291

[13] SEX ATTRACTANT IN A BROWN ALGA - CHEMICAL STRUCTURE [J].

MULLER, DG ;

JAENICKE, L ;

DONIKE, M ;

AKINTOBI, T .

SCIENCE, 1971, 171 (3973) :815-&

[14] STEREOCHEMICAL STUDIES ON ALGAL PHEROMONE BIOSYNTHESIS - A MODEL STUDY WITH THE FLOWERING PLANT SENECIO-ISATIDEUS (ASTERACEAE) [J].

NEUMANN, C ;

BOLAND, W .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1990, 191 (02) :453-459

[15]

PANTKE S, 1992, THESIS U KARLSRUHE

[16] PERICYCLIC-REACTIONS IN NATURE - EVIDENCE FOR A SPONTANEOUS [1.7]-HYDROGEN SHIFT AND AN 8-PI-E ELECTROCYCLIC RING-CLOSURE IN THE BIOSYNTHESIS OF OLEFINIC HYDROCARBONS FROM MARINE BROWN-ALGAE (PHAEOPHYCEAE) [J].

POHNERT, G ;

BOLAND, W .

TETRAHEDRON, 1994, 50 (34) :10235-10244

[17]

POHNERT G, 1995, IN PRESS TETRAHEDRON

[18] LOW-TEMPERATURE THERMAL AND PHOTOCHEMICAL FORMATION OF DIALLYLIC 1,3-DIRADICALS - COPE REARRANGEMENT OF CIS-1,2-DIVINYLCYCLOPROPANE [J].

SCHNEIDER, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (10) :707-708

[19] 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

[20] BIOSYNTHESIS OF PHEROMONES IN FEMALE GAMETES OF MARINE BROWN-ALGAE (PHAEOPHYCEAE) [J].

STRATMANN, K ;

BOLAND, W ;

MULLER, DG .

TETRAHEDRON, 1993, 49 (18) :3755-3766