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

Fanny Cherblanc, Ya-Pei Lo, Ewoud De Gussem, Laura Alcazar-Fuoli, Elaine Bignell, Yanan He, Nadine Chapman-Rothe, Patrick Bultinck UGent, Wouter A Herrebout, Robert Brown, et al. (2011) CHEMISTRY-A EUROPEAN JOURNAL. 17(42). p.11868-11875
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
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
journal title
CHEMISTRY-A EUROPEAN JOURNAL
Chem.-Eur. J.
volume
17
issue
42
pages
11868 - 11875
Web of Science type
Article
Web of Science id
000297314100024
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
5.925 (2011)
JCR rank
18/149 (2011)
JCR quartile
1 (2011)
ISSN
0947-6539
DOI
10.1002/chem.201101129
project
HPC-UGent: the central High Performance Computing infrastructure of Ghent University
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1972626
handle
http://hdl.handle.net/1854/LU-1972626
date created
2011-12-22 09:19:58
date last changed
2018-01-29 12:12:59
@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},
}

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.