Title
On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy : desulfurization of epidithiodioxopiperazine fungal metabolites On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy : desulfurization of epidithiodioxopiperazine fungal metabolites
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
Chemistry: a European journal. - Weinheim
Volume/pages
17(2011) :42 , p. 11868-11875
ISSN
0947-6539
ISI
000297314100024
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
Isolation and semisynthetic modification of the fungal metabolite chaetocin gave access to a desulfurized analogue of this natural product. Detailed chiroptical studies, comparing experimentally obtained optical rotation values, electronic circular dichroism spectra, and vibrational circular dichroism spectra to computationally simulated ones, reveal the desulfurization of chaetocin to unambiguously proceed with retention of configuration. Consideration of the plausible mechanisms for this process highlighted inconsistencies in the stereochemical assignment of related molecules in the literature. This in turn allowed the stereochemical reassignment of the natural product analogue dethiodehydrogliotoxin.
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