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Final Elucidation of the Absolute Configuration of the Signal Metabolite Hormaomycin
Author(s) -
Zlatopolskiy Boris D.,
Loscha Karin,
Alvermann Petra,
Kozhushkov Sergei I.,
Nikolaev Sergej V.,
Zeeck Axel,
de Meijere Armin
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200400406
Subject(s) - absolute configuration , stereocenter , metabolite , chemistry , absolute (philosophy) , deuterium , stereochemistry , high performance liquid chromatography , molecule , biosynthesis , chromatography , enantioselective synthesis , organic chemistry , biochemistry , physics , catalysis , quantum mechanics , enzyme , philosophy , epistemology
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.