Final Elucidation of the Absolute Configuration of the Signal Metabolite Hormaomycin

✍ Scribed by Boris D. Zlatopolskiy; Karin Loscha; Petra Alvermann; Sergei I. Kozhushkov; Sergej V. Nikolaev; Axel Zeeck; Armin de Meijere

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 406 KB
• Volume: 10
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200400406

✦ Synopsis

Abstract

The complete absolute configuration of hormaomycin 1 a has been established by HPLC and HPLC/MS experiments with appropriately derivatized 4‐propylprolines, (2__S__,4__S__)‐6 and (2__R__,4__R__)‐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, (2__S__)‐3,3‐[D~2~]15 and (2__S__)‐2,2′‐[D~2~]15, and 4‐(Z)‐propenylproline 2′,4‐[D~2~]‐(2__S__,4__R__)‐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.