Structure-based predictions of 1H NMR chemical shifts of sesquiterpene lactones using neural networks

Fernando Batista Da Costa, Yuri Binev, Johann Gasteiger, João Aires-De-Sousa

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The prediction of 1H NMR chemical shifts of CH n protons of the sesquiterpene lactones 1 and 2 using neural networks was performed and the results were highly accurate. This method has the ability to assign CH 2 diastereotopic protons of 3D structures. In this work the prediction of 1H NMR chemical shifts of CH n protons of sesquiterpene lactones by means of neural networks is described. This method is based on the incorporation of experimental chemical shifts of protons of sesquiterpene lactones as additional memory of an associative neural network system previously trained with chemical shifts of other organic compounds. One advantage of this method is its ability to distinguish between CH 2 diastereotopic protons belonging to rigid substructures since stereochemistry is considered. This is achieved via the automatic conversion of the 2D structure diagram into a 3D molecular structure. The predicted 1H NMR chemical shifts of the sesquiterpene lactones showed a high level of accuracy. This is the first report on a fully automatic proton assignment of structures of sesquiterpene lactones of an accuracy that allows its use in structure elucidation.

Original languageEnglish
Pages (from-to)6931-6935
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number37
DOIs
Publication statusPublished - 6 Sep 2004

Keywords

  • H NMR spectroscopy
  • Chemical shift prediction
  • Neural networks
  • Sesquiterpene lactones
  • Structure-based prediction.

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