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

(2011) CHEMISTRY-A EUROPEAN JOURNAL. 17(42). p.11868-11875
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HPC-UGent: the central High Performance Computing infrastructure of Ghent University
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
desulfurization, OPTICAL-ROTATORY POWER, VIBRATIONAL CIRCULAR-DICHROISM, vibrational spectroscopy, natural products, circular dichroism, configuration determination, ABSOLUTE-CONFIGURATION, STRUCTURE ELUCIDATION, REVISED STRUCTURE, CHAETOMIUM, CHAETOCIN, VCD, EPIPOLYTHIODIOXOPIPERAZINES, TRIPHENYLPHOSPHINE

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Citation

Please use this url to cite or link to this publication:

Chicago
Cherblanc, Fanny, Ya-Pei Lo, Ewoud De Gussem, Laura Alcazar-Fuoli, Elaine Bignell, Yanan He, Nadine Chapman-Rothe, et al. 2011. “On the Determination of the Stereochemistry of Semisynthetic Natural Product Analogues Using Chiroptical Spectroscopy: Desulfurization of Epidithiodioxopiperazine Fungal Metabolites.” Chemistry-a European Journal 17 (42): 11868–11875.
APA
Cherblanc, F., Lo, Y.-P., De Gussem, E., Alcazar-Fuoli, L., Bignell, E., He, Y., Chapman-Rothe, N., et al. (2011). On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: desulfurization of epidithiodioxopiperazine fungal metabolites. CHEMISTRY-A EUROPEAN JOURNAL, 17(42), 11868–11875.
Vancouver
1.
Cherblanc F, Lo Y-P, De Gussem E, 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. CHEMISTRY-A EUROPEAN JOURNAL. 2011;17(42):11868–75.
MLA
Cherblanc, Fanny, Ya-Pei Lo, Ewoud De Gussem, et al. “On the Determination of the Stereochemistry of Semisynthetic Natural Product Analogues Using Chiroptical Spectroscopy: Desulfurization of Epidithiodioxopiperazine Fungal Metabolites.” CHEMISTRY-A EUROPEAN JOURNAL 17.42 (2011): 11868–11875. Print.
@article{1972626,
  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       = {Cherblanc, Fanny and Lo, Ya-Pei and De Gussem, Ewoud and Alcazar-Fuoli, Laura and Bignell, Elaine and He, Yanan and Chapman-Rothe, Nadine and Bultinck, Patrick and Herrebout, Wouter A and Brown, Robert and Rzepa, Henry S and Fuchter, Matthew J},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {desulfurization,OPTICAL-ROTATORY POWER,VIBRATIONAL CIRCULAR-DICHROISM,vibrational spectroscopy,natural products,circular dichroism,configuration determination,ABSOLUTE-CONFIGURATION,STRUCTURE ELUCIDATION,REVISED STRUCTURE,CHAETOMIUM,CHAETOCIN,VCD,EPIPOLYTHIODIOXOPIPERAZINES,TRIPHENYLPHOSPHINE},
  language     = {eng},
  number       = {42},
  pages        = {11868--11875},
  title        = {On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: desulfurization of epidithiodioxopiperazine fungal metabolites},
  url          = {http://dx.doi.org/10.1002/chem.201101129},
  volume       = {17},
  year         = {2011},
}

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