Resolution and chiroptical properties of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline (TaClo) and related compounds: quantum chemical CD calculations and X-ray diffraction analysis |
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| Authors: | Gerhard Bringmann Doris Feineis Katja Maksimenka Kim Messer Klaus-Peter Gulden Karl Peters |
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| Affiliation: | a Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany
b Max-Planck-Institut für Festkörperforschung, Heisenbergstraβe 1, D-70506 Stuttgart, Germany |
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| Abstract: | Separation and stereochemical attribution of the two enantiomers of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline (TaClo) has been achieved by applying chromatography on a chiral phase HPLC column in hyphenation with circular dichroism (CD) spectroscopy (LC-CD coupling). Assignment of the absolute configuration of TaClo and its N-methyl analog has been achieved by quantum chemical CD calculations and has finally been confirmed by single-crystal X-ray diffraction analyses of the two enantiomers of N-formyl-TaClo as obtained in enantiomerically pure form by crystallization. |
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| Keywords: | Chloral-derived tetrahydro-β-carbolines 1-Trichloromethyl-1,2,3,4-tetrahydro-β-carboline (TaClo) Enantiomeric resolution Absolute configuration Circular dichroism LC-CD coupling Quantum chemical CD calculations Crystal structures |
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