A Spectroscopic Study of Colchicine in the Solid State and in Solution by Multinuclear Magnetic Resonance and Vibrational Circular Dichroism

Albert Virgili Moya, Ma Mar Quesada-Moreno, Juan Ramon Aviles-Moreno, Juan Jesus Lopez-Gonzalez, M. Angeles Garcac, Rosa M. Claramunt, M. Rosario Torresd, M. Luisa Jimenoe, Felipe Reviriego, Ibon Alkorta, José Elgueroe

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

Abstract

Although almost 200-years-old, several unknown aspects remain to be explored of colchicine, the unique available drug for acute flares of gout. In this article, we report density-functional theory (DFT) studies of geometry, energy, and NMR; 1H-, 13C-, and 15N-NMR chemical shifts and some spin-spin coupling constants, including the complete analysis of the saturated part (ring B); the assignment of both enantiomers by NMR using a chiral solvating agent; solid-state NMR experiments of the different forms of natural and racemic colchicine, and IR and vibrational circular dichroism (VCD) studies of these same forms. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.
Original languageEnglish
Pages (from-to)471-490
JournalHelvetica Chimica Acta
Volume97
Issue number97
DOIs
Publication statusPublished - 1 Jan 2014

Keywords

  • Chiral solvating agents
  • Colchicine
  • Racemization
  • Vibrational circular dichroism (VCD)
  • X-Ray crystallography

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