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

doi:10.1021/acs.orglett.6b00044

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

Unite de recherche en chimie physique, theorique et structurale

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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).

langue originale	Anglais
Pages (de - à)	780-783
Nombre de pages	4
journal	Organic Letters
Volume	18
Numéro de publication	4
Les DOIs	https://doi.org/10.1021/acs.orglett.6b00044
Etat de la publication	Publié - 19 févr. 2016

Accès au document

10.1021/acs.orglett.6b00044

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Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager), Aprile, C. (!!Manager) & Fusaro, L. (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique

CCDC 1401228: Experimental Crystal Structure Determination
Čikoš, A. (Contributeur), Triballeau, N. (Contributeur), Hubbard, P. A. (Contributeur), Žiher, D. (Contributeur), Stouten, P. F. W. (Contributeur), Doyon, J. G. P. O. (Contributeur), Deschrijver, T. (Contributeur), Wouters, J. (Contributeur), Lépine, R. H. M. (Contributeur) & Saniere, L. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2016
DOI: 10.5517/cc1j12xk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc1j12xk&sid=DataCite
Ensemble de données

Contient cette citation

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title = "Reinvestigation of the Branimycin Stereochemistry at Position 17-C",

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).",

author = "Ana {\v C}iko{\v s} and Nicolas Triballeau and Hubbard, {Paul A.} and Dinko {\v Z}iher and Stouten, {Pieter F W} and Doyon, {Julien G P O} and Tiny Deschrijver and Johan Wouters and L{\'e}pine, {Renaud H M} and Laurent Saniere",

year = "2016",

month = feb,

day = "19",

doi = "10.1021/acs.orglett.6b00044",

language = "English",

volume = "18",

pages = "780--783",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Reinvestigation of the Branimycin Stereochemistry at Position 17-C

AU - Čikoš, Ana

AU - Triballeau, Nicolas

AU - Hubbard, Paul A.

AU - Žiher, Dinko

AU - Stouten, Pieter F W

AU - Doyon, Julien G P O

AU - Deschrijver, Tiny

AU - Wouters, Johan

AU - Lépine, Renaud H M

AU - Saniere, Laurent

PY - 2016/2/19

Y1 - 2016/2/19

N2 - 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).

AB - 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).

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U2 - 10.1021/acs.orglett.6b00044

DO - 10.1021/acs.orglett.6b00044

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AN - SCOPUS:84959019294

SN - 1523-7060

VL - 18

SP - 780

EP - 783

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Reinvestigation of the Branimycin Stereochemistry at Position 17-C

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 1401228: Experimental Crystal Structure Determination

Contient cette citation