Final Elucidation of the Absolute Configuration of the Signal Metabolite Hormaomycin (pages 4708–4717)
Boris D. Zlatopolskiy, Karin Loscha, Petra Alvermann, Sergei I. Kozhushkov, Sergej V. Nikolaev, Axel Zeeck and Armin de Meijere
Version of Record online: 20 AUG 2004 | DOI: 10.1002/chem.200400406
Final elucidation of the absolute configuration of hormaomycin 1 a has been accomplished by appropriate HPLC and HPLC/MS as well as feeding experiments with enantiomerically pure samples of the deuterium-labeled unique amino acids 3-(2′-nitrocyclopropyl)alanine and 4-(Z)-propenylproline. The latter were prepared for the first time and allowed one to unequivocally assign the hitherto unknown absolute configurations of the last four stereocenters in hormaomycin 1 a. As a bonus, some new information about the biosynthesis of this molecule has also been gathered.