Abstract
A robust system for automatic processing and assignment of raw 13C and 1H NMR data DP4-AI has been developed and integrated into our computational organic molecule structure elucidation workflow. Starting from a molecular structure with undefined stereochemistry or other structural uncertainty, this system allows for completely automated structure elucidation. Methods for NMR peak picking using objective model selection and algorithms for matching the calculated 13C and 1H NMR shifts to peaks in noisy experimental NMR data were developed. DP4-AI achieved a 60-fold increase in processing speed, and near-elimination of the need for scientist time, when rigorously evaluated using a challenging test set of molecules. DP4-AI represents a leap forward in NMR structure elucidation and a step-change in the functionality of DP4. It enables high-throughput analyses of databases and large sets of molecules, which were previously impossible, and paves the way for the discovery of new structural information through machine learning. This new functionality has been coupled with an intuitive GUI and is available as open-source software at https://github.com/KristapsE/DP4-AI.
Highlights
Structural elucidation of molecules is a challenging problem in both synthetic organic and natural product chemistry
Structural near isomers and diastereomers usually exhibit only subtle differences in their 1D NMR spectra, making determination of structure and relative stereochemistry very difficult. This can be addressed by additional NMR experiments such as nOeSY spectra or synthesizing isomers of the natural product and comparing the resulting observed NMR spectra with those published
The pairwise assignment algorithm (AA) represents the upper limit of DP4-AIs performance in this study as the NMR descriptions used by the pairwise AA have been meticulously written to remove any errors
Summary
Structural elucidation of molecules is a challenging problem in both synthetic organic and natural product chemistry. Structural near isomers (for example regioisomers and protecting group localisation) and diastereomers usually exhibit only subtle differences in their 1D NMR spectra, making determination of structure and relative stereochemistry very difficult. This can be addressed by additional NMR experiments such as nOeSY spectra or synthesizing isomers of the natural product and comparing the resulting observed NMR spectra with those published. DP4 analysis is powerful as it predicts the relative stereochemistry and other variations of the molecule, and using Bayes theorem gives a probability that each
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