Open AccessAbsolute chemical structure of the myxobacterial pheromone of Stigmatella aurantiaca that induces the formation of its fruiting body
Author(s) -
Morikawa Yuka,
Takayama Seiji,
Fudo Ryosuke,
Yamanaka Shigeru,
Mori Kenji,
Isogai Akira
Publication year - 1998
Publication title -
fems microbiology letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.899
H-Index - 151
eISSN - 1574-6968
pISSN - 0378-1097
DOI - 10.1111/j.1574-6968.1998.tb13123.x
Subject(s) - myxobacteria , absolute configuration , enantiomer , pheromone , chemistry , stereochemistry , stereoselectivity , botany , biology , biochemistry , bacteria , genetics , catalysis
Stigmatella aurantiaca , a species of myxobacteria, produces a novel extracellular signaling molecule, 8‐hydroxy‐2,5,8‐trimethyl‐4‐nonanone, which promotes its developmental cycle. To determine the absolute configuration of this pheromone, which contains one asymmetric carbon, we prepared the R ‐ and S ‐enantiomers by stereoselective synthesis. The synthesized R ‐ and S ‐enantiomers each showed nearly the same fruiting body‐inducing activities as the natural pheromone. Gas chromatography‐mass spectrometry (GC‐MS) analysis using a chiral capillary column revealed that the naturally‐produced pheromone is a mixture of both enantiomers.