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Publication . Article . 2018

Halterman Corroles and Their Use as a Probe of the Conformational Dynamics of the Inherently Chiral Copper Corrole Chromophore

Kolle E. Thomas; Laura J. McCormick; Daniel Carrié; Hugo Vazquez-Lima; Gérard Simonneaux; Abhik Ghosh;
Open Access
English
Published: 02 Apr 2018
Publisher: HAL CCSD
Abstract
© 2018 American Chemical Society. Halterman corroles have been synthesized for the first time from pyrrole and Halterman's aldehyde via Gryko's "water-methanol method". These were derivatized to the corresponding copper complexes and subsequently to the β-octabromo complexes. Electronic circular dichroism spectra were recorded for the enantiopure copper complexes, affording the first such measurements for the inherently chiral Cu corrole chromophore. Interestingly, for a given configuration of the Halterman substituents, X-ray crystallographic studies revealed both P and M conformations of the Cu-corrole core, proving that the substituents, even in conjunction with β-octabromination, are unable to lock the Cu-corrole core into a given chirality. The overall body of evidence strongly indicates a dynamic equilibrium between the P and M conformations. Such an interconversion, which presumably proceeds via saddling inversion, provides a rationale for our failure so far to resolve sterically hindered Cu corroles into their constituent enantiomers by means of chiral HPLC.
Subjects by Vocabulary

Microsoft Academic Graph classification: Chemistry Steric effects Corrole chemistry.chemical_compound Crystallography Enantiomer Enantiopure drug Chirality (chemistry) Chromophore Chiral column chromatography Pyrrole

Subjects

[CHIM.COOR]Chemical Sciences/Coordination chemistry, Inorganic & Nuclear Chemistry, Inorganic Chemistry, Chemical Engineering, Other Chemical Sciences, Inorganic Chemistry, Physical and Theoretical Chemistry, Physical Chemistry (incl. Structural)

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European Plate Observing System
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  • Project Code: 262229
  • Funding stream: FP7 | SP4 | INFRA
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The molecular mechanism of the reversible switch between cell proliferation and migration. The regulatory function of the ERK pathway and ERK pathway scaffold RACK1
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