Natural products dereplication by diffusion ordered NMR spectroscopy (DOSY)
| العنوان: | Natural products dereplication by diffusion ordered NMR spectroscopy (DOSY) |
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| المؤلفون: | Anthony R. Carroll, Guy Kleks, Darren C. Holland, Joshua Porter |
| المصدر: | Chemical Science |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | chemistry.chemical_classification, 010405 organic chemistry, Hydrogen bond, Ms analysis, General Chemistry, Polymer, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, 01 natural sciences, Organic compound, 0104 chemical sciences, Chemistry, Molecular geometry, Molar volume, chemistry, Computational chemistry, Diffusion (business) |
| الوصف: | Diffusion-ordered NMR spectroscopy (DOSY) can be used to analyze mixtures of compounds since resonances deriving from different compounds are distinguished by their diffusion coefficients (D). Previously, DOSY has mostly been used for organometallic and polymer analysis, we have now applied DOSY to investigate diffusion coefficients of structurally diverse organic compounds such as natural products (NP). The experimental Ds derived from 55 diverse NPs has allowed us to establish a power law relationship between D and molecular weight (MW) and therefore predict MW from experimental D. We have shown that D is also affected by factors such as hydrogen bonding, molar density and molecular shape of the compound and we have generated new models that incorporate experimentally derived variables for these factors so that more accurate predictions of MW can be calculated from experimental D. The recognition that multiple physicochemical properties affect D has allowed us to generate a polynomial equation based on multiple linear regression analysis of eight calculated physicochemical properties from 63 compounds to accurately correlate predicted D with experimental D for any known organic compound. This equation has been used to calculate predicted D for 217 043 compounds present in a publicly available natural product database (DEREP-NP) and to dereplicate known NPs in a mixture based on matching of experimental D and structural features derived from NMR analysis with predicted D and calculated structural features in the database. These models have been validated by the dereplication of a mixture of two known sesquiterpenes obtained from Tasmannia xerophila and the identification of new alkaloids from the bryozoan Amathia lamourouxi. These new methodologies allow the MW of compounds in mixtures to be predicted without the need for MS analysis, the dereplication of known compounds and identification of new compounds based solely on parameters derived by DOSY NMR. We report accurate DOSY NMR based molecular weight and diffusion coefficient prediction tools. These tools can be used to dereplicate known natural products from databases using structurally rich NMR data as a surrogate for mass spectrometric data. |
| تدمد: | 2041-6539 2041-6520 |
| DOI: | 10.1039/d1sc02940a |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c774433730a4ff85d593b39c69e2cc43 https://doi.org/10.1039/d1sc02940a |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....c774433730a4ff85d593b39c69e2cc43 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 20416539 20416520 |
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| DOI: | 10.1039/d1sc02940a |