title: Recent advances in the structure elucidation of small organic molecules by the LSD software.
abstract: The LSD software proposes the structures of small organic molecules that fit with structural constraints from 1D and 2D NMR spectroscopy. Its initial design introduced limits that needed to be eliminated to extend its scope and help its users choose the most likely structure among those proposed. The LSD software code has been improved, so that it recognizes a wider set of atom types to build molecules. More flexibility has been given in the interpretation of 2D NMR data, including the automatic detection of very long-range correlations. A program named pyLSD was written to deal with problems in which atom types are ambiguously defined. It also provides a (13)C NMR chemical shift-based solution ranking algorithm. PyLSD was able to propose the correct structure of hexacyclinol, a natural product whose structure determination has been highly controversal. The solution was ranked first within a list of ten structures that were produced by pyLSD from the literature NMR data. The structure of an aporphin natural product was determined by pyLSD, taking advantage of the possibility of handling electrically charged atoms. The structure generation of the insect antifeedant azadirachtin by LSD was reinvestigated by pyLSD, considering that three (13)C resonances did not lead to univocal hybridization states.
authors.affiliation: Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, Université de Reims-Champagne-Ardenne, BP 1039, 51687 REIMS Cedex 2, France.
authors.forename: Bertrand
authors.initials: B
authors.lastname: Plainchont
authors.forename: Vicente
authors.initials: V
authors.lastname: de Paulo Emerenciano
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Nuzillard
mesh_terms: D000465:Algorithms; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D012984:Software
chemical_list: D004852:Epoxy Compounds; D011083:Polycyclic Compounds; C469535:hexacyclinol
keywords: chemical shift prediction; computer software; correlation NMR; natural products; structure elucidation