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On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: desulfurization of epidithiodioxopiperazine fungal metabolites

Author
Organization
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.
Keywords
VCD chirality

Citation

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Chicago
De Gussem, Ewoud, Fanny Cherblanc, Y Lo, L Alcazar-Fuoli, E Bignell, Yanan He, N Chapman-Rothe, et al. 2012. “On the Determination of the Stereochemistry of Semisynthetic Natural Product Analogues Using Chiroptical Spectroscopy: Desulfurization of Epidithiodioxopiperazine Fungal Metabolites.” In Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts.
APA
De Gussem, E., Cherblanc, F., Lo, Y., Alcazar-Fuoli, L., Bignell, E., He, Y., Chapman-Rothe, N., et al. (2012). On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: desulfurization of epidithiodioxopiperazine fungal metabolites. Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts. Presented at the Vibrational Optical Activity : Interplay of Theory and Experiment.
Vancouver
1.
De Gussem E, Cherblanc F, Lo Y, Alcazar-Fuoli L, Bignell E, He Y, et al. On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: desulfurization of epidithiodioxopiperazine fungal metabolites. Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts. 2012.
MLA
De Gussem, Ewoud, Fanny Cherblanc, Y Lo, et al. “On the Determination of the Stereochemistry of Semisynthetic Natural Product Analogues Using Chiroptical Spectroscopy: Desulfurization of Epidithiodioxopiperazine Fungal Metabolites.” Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts. 2012. Print.
@inproceedings{3002715,
  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.},
  author       = {De Gussem, Ewoud and Cherblanc, Fanny and Lo, Y and Alcazar-Fuoli, L and Bignell, E and He, Yanan and Chapman-Rothe, N and Bultinck, Patrick and Herrebout, Wouter and Brown, R and Rzepa, Henry and Fuchter, Matthew},
  booktitle    = {Vibrational Optical Activity : Interplay of Theory and Experiment, Abstracts},
  keyword      = {VCD chirality},
  language     = {eng},
  location     = {Pisa, Italy},
  title        = {On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: desulfurization of epidithiodioxopiperazine fungal metabolites},
  year         = {2012},
}