Tutorial for the structure elucidation of small molecules by means of the LSD software.

Fiche publication

Date publication

mai 2017

Journal

Magnetic resonance in chemistry : MRC

Auteurs

Membres identifiés du Cancéropôle Est :
Dr NUZILLARD Jean-Marc

Tous les auteurs :
Nuzillard JM, Plainchont B

Lien Pubmed

https://www.ncbi.nlm.nih.gov/pubmed/28543725

Résumé

Automatic structure elucidation of small molecules by means of the "Logic for Structure Elucidation" software (LSD) is introduced in the context of the automatic exploitation of chemical shift correlation data and with minimal input from chemical shift values. The first step in solving a structural problem by means of LSD is the extraction of pertinent data from the 1D and 2D spectra. This operation requires the labeling of the resonances and of their correlations; its reliability highly depends on the quality of the spectra. The combination of COSY, HSQC and HMBC spectra results in proximity relationships between non-hydrogen atoms that are associated in order to build the possible solutions of a problem. A simple molecule, camphor, serves as an example for the writing of an LSD input file and to show how solution structures are obtained. An input file for LSD must contain a non-ambiguous description of each atom, or atom status, which includes the chemical element symbol, the hybridization state, the number of bound hydrogen atoms and the formal electric charge. In case of atom status ambiguity, the pyLSD program performs clarification by systematically generating the status of the atoms. PyLSD also proposes the use of the nmrshiftdb algorithm in order to rank the solutions of a problem according to the quality of the fit between the experimental carbon-13 chemical shifts and the ones predicted from the proposed structures. To conclude, some hints toward future uses and developments of computer-assisted structure elucidation by LSD are proposed.