Automated Interpretation of NMR Spectra for Small Organic Molecules in Solution

Nuzillard, Jean-Marc

doi:10.1002/9780470034590.emrstm1384

Cited by 12 publications

(7 citation statements)

References 37 publications

(31 reference statements)

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“…Reporting correct structures and NMR parameter assignments is an important part of the activity of organic chemists as the corresponding data constitute a basis for the identification of known molecules during dereplication 29 and of new molecules during structure elucidation. 30 At the beginning of the application of NMR to organic molecules, the attention was focused on the reporting of 1D NMR parameters, which were the only ones available back then. The advent of 2D NMR made the 1D spectra interpretation more reliable when dealing with compounds of constantly increasing molecular complexity.…”

Section: Relationships Between Structures and Nmr Parametersmentioning

confidence: 99%

Advanced NMR-Based Structural Investigation of Glucosinolates and Desulfoglucosinolates

et al. 2018

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Glucosinolates (GLs) constitute a class of plant secondary metabolites that are characteristic of the order Brassicales. They each contain a common hydrophilic moiety connected to a mostly hydrophobic side chain whose constitution is the most frequent structural variant. Their transformations by myrosinases lead to intensively studied and highly reactive compounds of biological relevancy. In other respects, the enzymatic desulfation of GLs produces derivatives (DS-GLs) that are useful for GL analysis. A collection of 31 compounds, GLs and DS-GLs, representing 17 different side chains was established in order to report accurate descriptions of the molecules' H-,C-, and N-NMR parameters. The descriptions of theH-NMR spectra were achieved using the PERCH software, which accurately analyzed the complex coupling patterns that arose from strongly coupled nuclei. The chemical shift assignments were supported by 2D COSY, HSQC, and HMBC spectra. The impact of desulfation and the influence of the nature of the side chains on the chemical shift values are discussed. The results of the spectroscopic analysis and the 3D chemical-structure models of the studied molecules were grouped in structure-and-data-format (SDF) files. The NMR parameters were also collected in a simple text file, a spreadsheet file, and a relational database.

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Section: Relationships Between Structures and Nmr Parametersmentioning

confidence: 99%

Advanced NMR-Based Structural Investigation of Glucosinolates and Desulfoglucosinolates

et al. 2018

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“…Several reviews and books have been published on automatic structure elucidation, which is often referred as computer-assisted structure elucidation (CASE) [21–23]. Recently developed CASE programs, such as ACD/Structure Elucidator and Bruker CMC-se, are already able to automatize many of the steps required for the analysis and interpretation of standard one- and two-dimensional, respectively) NMR data, with minimal human interference, such as confirmation of the automatically-generated correlation table.…”

Section: Nmr Spectroscopymentioning

confidence: 99%

Computationally-assisted discovery and structure elucidation of natural products

Nugroho

Morita

2019

J Nat Med

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Computer hardware development coupled with the development of quantum chemistry, new computational models and algorithms, and user-friendly interfaces have lowered the barriers to the use of computation in the discovery and structure elucidation of natural products. Consequently, the use of computational chemistry software as a tool to discover and determine the structure of natural products has become more common in recent years. In this review, we provide several examples of recent studies that used computer technology to facilitate the discovery and structure determination of various natural products.

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“…However, the notoriously low sensitivity of the INADEQUATE experiment means that high sample concentrations and/or long acquisition times are necessary. In the vast majority of small organic molecules, the structure can be established from three basic 1 H-detected 2D NMR experiments [121][122][123][124][125] -HSQC, HMBC and COSY. As discussed in the previous section, the HSQC, HMBC and COSY modules can be linked into multiple NOAH supersequences, such as NOAH-3 SBC, NOAH-3 BSC, NOAH-4 SBCN, NOAH-4 BSCN, NOAH-4 MSBC, NOAH-5 MSBCN and similar.…”

Section: Noah Supersequences For Structure Elucidationmentioning

confidence: 99%