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Pheromone Synthesis, CLXXXV Synthesis of the Analogues of Lurlenic Acid with a Modified Sugar Part: Chlamydomonas responds only to the D ‐xyloside
Author(s) -
Takanashi ShinIchi,
Mori Kenji
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970606
Subject(s) - chemistry , pheromone , sugar , stereochemistry , chlamydomonas , organic chemistry , biochemistry , botany , biology , gene , mutant
Abstract Six analogues of lurlenic acid [(4 E ,8 E ,12 E )‐14‐[2′‐hydroxy‐3′,4′‐dimethyl‐5′‐(1″‐β‐ D ‐xylopyranosyloxy)phenyl]‐4,8,12‐trimethyltetradeca‐4,8,12‐trienoic acid( 1 )], the mating pheromone of Chlamydomonas allensworthii , were synthesized as E/Z mixtures ( E/Z = 3:2) at C‐12. They possess a tetrahydropyranyl ( 1a ), β‐ L ‐xylopyranosyl ( 1b ), β‐ D ‐glucopyranosyl ( 1e ) or β‐ D ‐arabinopyranosyl ( 1f ) group, respectively, as the sugar part. Only lurlenic acid ( 1 ) was bioactive as the pheromone.