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Strength by Joining Methods: Combining Synthesis with NMR, IR, and Vibrational Circular Dichroism Spectroscopy for the Determination of the Relative Configuration in Hemicalide
Author(s) -
De Gussem Ewoud,
Herrebout Wouter,
Specklin Simon,
Meyer Christophe,
Cossy Janine,
Bultinck Patrick
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404822
Subject(s) - stereocenter , circular dichroism , vibrational circular dichroism , absolute configuration , spectroscopy , chemistry , infrared spectroscopy , nuclear magnetic resonance spectroscopy , stereochemistry , protein subunit , crystallography , organic chemistry , physics , catalysis , biochemistry , quantum mechanics , enantioselective synthesis , gene
The relative configuration of a key subunit of hemicalide, a recently isolated, highly bioactive marine natural product having potent antiproliferative activity against a panel of human cancer cell lines, was assigned by combining stereocontrolled synthesis of model substrates with NMR, IR, and vibrational circular dichroism (VCD) spectroscopy. The assignment of the absolute configuration of asymmetric carbon center C42 in two structurally complex epimeric substructures containing six stereocenters by VCD analysis illustrates the power and reliability of combining methods.