Abstract
Over the past decades, different software programs have been developed for the Computer-Assisted Structure Elucidation (CASE) with NMR data using with various approaches. WebCocon is one of them that has been continuously improved over the past 20 years. Here, we present the inclusion of CH correlations (-HMBC) in the HMBC interpretation of Cocon and NOE data in WebCocon. The -HMBC data is used during the structure generation process, while the NOE data is used in post-processing of the results. The marine natural product oxocyclostylidol was selected to demonstrate WebCocon’s enhanced HMBC data processing capabilities. A systematic study of the CH correlations of oxocyclostylidol was performed. The application of NOEs in CASE is demonstrated using the NOE correlations of the diterpene pyrone asperginol A known from the literature. As a result, we obtained a conformation that corresponds very well to the existing X-ray structure.
Highlights
In order to address this question, W EB C OCON can generate a complete theoretical NMR correlation data set (COSY, HMBC, NHMBC, and ADEQ data) for a molecule. These data can be submitted to the W EB C OCON server for a structure elucidation [32]
The results shown clearly indicate that the fastest way to achieve a small set of suggested constitutions is the exclusion of 4 J-HMBC correlations
There are not many examples reported in the literature for either case
Summary
Different software programs have been developed for the ComputerAssisted Structure Elucidation (CASE) with NMR data using with various approaches. We present the inclusion of 4 J CH correlations (4 J-HMBC) in the HMBC interpretation of C OCON and NOE data in. The 4 J-HMBC data is used during the structure generation process, while the NOE data is used in post-processing of the results. One- and two-dimensional NMR experiments constitute the backbone of structure elucidation of unknown compounds in Organic Chemistry. Following the identification of hydrogen-carbon and hydrogen-nitrogen bonds in the HSQC-based suites of experiments, 1 H,13 C- and 1 H,15 N-HMBC-derived connectivity data will allow to propose the constitution of a new compound. The intensity of an HMBC peak will not always exclude its interpretation as a long-range correlation (more than three bonds)
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