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

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	780-783
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.6b00044
Publication status	Published - 19 Feb 2016

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10.1021/acs.orglett.6b00044

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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",

publisher = "American Chemical Society",

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TY - JOUR

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).

UR - http://www.scopus.com/inward/record.url?scp=84959019294&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b00044

DO - 10.1021/acs.orglett.6b00044

M3 - Article

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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

Abstract

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Physical Chemistry and characterization(PC2)

CCDC 1401228: Experimental Crystal Structure Determination

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Reinvestigation of the Branimycin Stereochemistry at Position 17-C

Abstract

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Equipment

Physical Chemistry and characterization(PC2)

Datasets

CCDC 1401228: Experimental Crystal Structure Determination

Cite this