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Research Article

Validation of Structural Proposals by Substructure Analysis and ¹³C NMR Chemical Shift Prediction

Jens Meiler,^† Erdogan Sanli,^† Jochen Junker,^† Reinhard Meusinger,^‡ Thomas Lindel,^§ Martin Will, Walter Maier, and Matthias Köck*

Alfred-Wegener-Institut fr Polar- und Meeresforschung, Am Handelshafen 12, D-27570 Bremerhaven, Germany, Institut fr Organische Chemie, J. W. Goethe-Universitt Frankfurt, Marie-Curie-Strasse 11, D-60439 Frankfurt, Germany, Institut fr Organische Chemie, Universitt Mainz, D-55099 Mainz, Germany, Department Chemie, Universitt Mnchen, Butenandtstrasse 5-13, D-81377 Mnchen, Germany, and BASF AG, D-67056 Ludwigshafen, Germany

J. Chem. Inf. Comput. Sci., 2002, 42 (2), pp 241–248

DOI: 10.1021/ci010294n

Publication Date (Web): March 8, 2002

†

Institut für Organische Chemie, Universität Frankfurt.

‡

Institut für Organische Chemie, Universität Mainz.

Department Chemie, Universität München.

BASF AG, Ludwigshafen.

Corresponding author phone: +49-471-4831-1497; fax: +49-471-4831-1425; e-mail: mkoeck@awi-bremerhaven.de.

Alfred-Wegener-Institut für Polar-und Meeresforschung, Bremerhaven.

Abstract

The 2D NMR-guided computer program Cocon can be extremely valuable for the constitutional analysis of unknown compounds, if its results are evaluated by neural network-assisted ¹³C NMR chemical shift and substructure analyses. As instructive examples, data sets of four differently complex marine natural products were thoroughly investigated. As a significant step towards a true automated structure elucidation, it is shown that the primary Cocon output can be safely diminished to less than 1% of its original size without losing the correct structural proposal.

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