Reinvestigation of the Branimycin Stereochemistry at Position 17-C

Ana Čikoš, Nicolas Triballeau, Paul A. Hubbard, Dinko Žiher, Pieter F W Stouten, Julien G P O Doyon, Tiny Deschrijver, Johan Wouters, Renaud H M Lépine, Laurent Saniere

Research output: Contribution to journalArticle

Abstract

A conformational study of branimycin was performed using single-crystal X-ray crystallography to characterize the solid-state form, while a combination of NMR spectroscopy and molecular modeling was employed to gain information about the solution structure. Comparison of the crystal structure with its solution counterpart showed no significant differences in conformation, confirming the relative rigidity of the tricyclic system. However, these experiments revealed that the formerly proposed stereochemistry of branimycin at 17-C should be revised. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)780-783
Number of pages4
JournalOrganic Letters
Volume18
Issue number4
DOIs
Publication statusPublished - 19 Feb 2016

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Stereochemistry
stereochemistry
Molecular modeling
X ray crystallography
X Ray Crystallography
rigidity
Rigidity
Nuclear magnetic resonance spectroscopy
crystallography
Conformations
Magnetic Resonance Spectroscopy
Crystal structure
Single crystals
solid state
nuclear magnetic resonance
crystal structure
single crystals
spectroscopy
x rays
Experiments

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Čikoš, A., Triballeau, N., Hubbard, P. A., Žiher, D., Stouten, P. F. W., Doyon, J. G. P. O., ... Saniere, L. (2016). Reinvestigation of the Branimycin Stereochemistry at Position 17-C. Organic Letters, 18(4), 780-783. https://doi.org/10.1021/acs.orglett.6b00044
Čikoš, Ana ; Triballeau, Nicolas ; Hubbard, Paul A. ; Žiher, Dinko ; Stouten, Pieter F W ; Doyon, Julien G P O ; Deschrijver, Tiny ; Wouters, Johan ; Lépine, Renaud H M ; Saniere, Laurent. / Reinvestigation of the Branimycin Stereochemistry at Position 17-C. In: Organic Letters. 2016 ; Vol. 18, No. 4. pp. 780-783.
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Čikoš, A, Triballeau, N, Hubbard, PA, Žiher, D, Stouten, PFW, Doyon, JGPO, Deschrijver, T, Wouters, J, Lépine, RHM & Saniere, L 2016, 'Reinvestigation of the Branimycin Stereochemistry at Position 17-C', Organic Letters, vol. 18, no. 4, pp. 780-783. https://doi.org/10.1021/acs.orglett.6b00044

Reinvestigation of the Branimycin Stereochemistry at Position 17-C. / Čikoš, Ana; Triballeau, Nicolas; Hubbard, Paul A.; Žiher, Dinko; Stouten, Pieter F W; Doyon, Julien G P O; Deschrijver, Tiny; Wouters, Johan; Lépine, Renaud H M; Saniere, Laurent.

In: Organic Letters, Vol. 18, No. 4, 19.02.2016, p. 780-783.

Research output: Contribution to journalArticle

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AU - Stouten, Pieter F W

AU - Doyon, Julien G P O

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AU - Saniere, Laurent

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Čikoš A, Triballeau N, Hubbard PA, Žiher D, Stouten PFW, Doyon JGPO et al. Reinvestigation of the Branimycin Stereochemistry at Position 17-C. Organic Letters. 2016 Feb 19;18(4):780-783. https://doi.org/10.1021/acs.orglett.6b00044