Journal
TETRAHEDRON
Volume 60, Issue 37, Pages 8143-8151Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.06.093
Keywords
chloral-derived tetrahydro-beta-carbolines; 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline (TaClo); enantiomeric resolution; absolute configuration; circular dichroism; LC-CD coupling; quantum chemical CD calculations; crystal structures
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Separation and stereochemical attribution of the two enantiomers of the neurotoxin 1-trichloromethyl-1,2,3,4-tetrahydro-beta-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. (C) 2004 Elsevier Ltd. All rights reserved.
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