Accurate Structural Elucidation of Samoquasine A and an Unknown Homologue Using a Computation-Based Machine Learning Protocol

The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historical...

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Published inThe journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Vol. 128; no. 24; pp. 4830 - 4837
Main Authors Wu, Anan, Chen, Qiwen, Feng, Jin, Ye, Jianliang, Xu, Xin
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.06.2024
Subjects
A: Structure, Spectroscopy, and Reactivity of Molecules and Clusters
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Summary:The structure of samoquasine A has long been a subject of controversy, which was resolved only upon its successful total synthesis. We examined the structures of the associated compounds using the state-of-the-art SVM-M protocol. The method accurately discriminated all putative structures historically attributed to samoquasine A from a pool of 48 isomeric structures, confirming that samoquasine A is indeed identical to perlolidine. Furthermore, by applying the SVM-M protocol to an additional pool of 67 isomeric structures, we successfully assigned a yet unknown natural product, initially misidentified as perlolidine, as a novel oxime, (E)-3H-cyclopenta­[c]­quinolin-3-one oxime, representing the first reported cyclone oxime-quinoline natural product.
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ISSN:1089-5639
1520-5215
1520-5215
DOI:10.1021/acs.jpca.4c02916