Chlamydomonas allensworthii

Lurlenic acid (23) is the sex pheromone produced by the female gametes of the green flagellate Chlamydomonas allensworthii to attract the male gametes. Mori s synthesis of 23 is summarized in Scheme 36 [59]. The aglycone part C was prepared by coupling A with B. 

Ista LK, Callow ME, Finlay JA, Coleman SE, Nolasco AC, Simons RH, Callow JA, Lopez GP (2004) Effect of substratum surface chemistry and surface energy on attachment of marine bacteria and algal spores. Appl Environ Microbiol 70 4151 4157 Jaenicke L, MamerFJ (1995) Lurlene, the sexual pheromone ofthe green flagellate Chlamydomonas allensworthii. Liebigs Ann 1995 1343-1345... 

Jaenicke L, Starr RC (1996) The lurlenes, a new class of plastoquinone-related mating pheromones from Chlamydomonas allensworthii (Chlorophyceae). Eur J Biochem 241 581-585 Janowitz GS, Kamykowski D (2006) Modeled Karenia brevis accumulation in the vicinity of a coastal nutrient front. Mar Ecol Prog Ser 314 49-59 Joint I, Tait K, Callow ME, Callow JA, Milton D, Williams P, Camara M (2002) Cell-to-cell communication across the prokaryote-eukaryote boundary. Science 298 1207 Kinzie RA (1974) Experimental infection of aposymbiotic gorgonian polyps with zooxanthellae. J Exp Mar Biol Ecol 15 335-342... 

In 1995 Starr el al. in the USA reported the chemoattraction of male gametes by female gametes of a new species of the green flagellate, Chlamydomonas allensworthii. The female-produced attractant pheromone was isolated and identified as 168 by Jaenicke and Marner in Germany. They coined the name lurlenic acid to 168, because they worked in Cologne near the Rock of Lorelei. The pheromone 168 attracts the male gametes at a concentration as low as 10-12M. 

Algae Low-molecular-weight unsaturated pheromones of cyclic or linear structure (for example 532 Da pentosylated hydroquinone in the case of Chlamydomonas allensworthii) [35, 92, 155]... 

Sexual pheromone of Chlamydomonas allensworthii. Glassy solid. 

In summary, as to Chlamydomoms allensworthii, its chemical communication system in connection with its sexuality was thus clarified. In contrast, as to Moewus observations on Chlamydomonas eugametos, things remain obscure even now. The elusive work of Moewus and Kuhn played the role of a magic lure to attract scientists of the next generation to study Chlamydomoms by their revolutionary proposal of sex attractants as a mixture of small molecules. 

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