Final elucidation of the absolute configuration of the signal metabolite hormaomycin.
The complete absolute configuration of hormaomycin 1 a has been established by HPLC and HPLC/MS experiments with appropriately derivatized 4-propylprolines, (2S,4S)-6 and (2R,4R)-6, as well as 4-(Z)-propenylprolines, cis-5 and trans-5, and also feeding experiments with enantiomerically pure samples of the deuterium-labeled 3-(2'-nitrocyclopropyl)alanine, (2S)-3,3-[D2]15 and (2S)-2,2'-[D2]15, and 4-(Z)-propenylproline 2',4-[D2]-(2S,4R)-5. The latter five amino acids 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.
Zlatopolskiy
Boris D
BD
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.
Loscha
Karin
K
Alvermann
Petra
P
Kozhushkov
Sergei I
SI
Nikolaev
Sergej V
SV
Zeeck
Axel
A
de Meijere
Armin
A
D047630:Depsipeptides / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015398:Signal Transduction / Q000502:physiology; D010456:Peptides, Cyclic
D047630:Depsipeptides; D007783:Lactones; C510371:hormaomycin; D010456:Peptides, Cyclic