STRUCTURE ELUCIDATION AND CHEMICAL SYNTHESIS OF STIGMOLONE, A NOVEL TYPE OF PROKARYOTIC PHEROMONE

Citation
We. Hull et al., STRUCTURE ELUCIDATION AND CHEMICAL SYNTHESIS OF STIGMOLONE, A NOVEL TYPE OF PROKARYOTIC PHEROMONE, Proceedings of the National Academy of Sciences of the United Statesof America, 95(19), 1998, pp. 11268-11273
Citations number
20
Categorie Soggetti
Multidisciplinary Sciences
ISSN journal
00278424
Volume
95
Issue
19
Year of publication
1998
Pages
11268 - 11273
Database
ISI
SICI code
0027-8424(1998)95:19<11268:SEACSO>2.0.ZU;2-K
Abstract
Approximately 2 mu mol of a novel prokaryotic pheromone, involved in s tarvation-induced aggregation and formation of fruiting bodies by the myxobacterium Stigmatella aurantiaca, mere isolated by a large-scale e lution procedure. The pheromone was purified by HPLC, and high-resolut ion MS, IR,H-1-NMR, and C-13-NMR mere used to identify the active subs tance as the hydroxy ketone 2,5,8-trimethyl-8-hydroxy -nonan-4-one, wh ich has been named stigmolone, The analysis was complicated by a solve nt-dependent equilibrium between stigmolone and the cyclic enol-ether ihydro-2,2,5-trimethyl-6-(2-methylpropyl)-2H-pyran formed by intramole cular nucleophilic attack of the S-OH group at the ketone C4 followed by loss of H2O. Both compounds were synthesized chemically, and their structures mere confirmed by NMR analysis, Natural and synthetic stigm olone have the same biological activity at cn. 1 nM concentration.