Phytochemical Study of Senecio volckmannii Assisted by CASE-3D with Residual Dipolar Couplings and Isotropic 1H/13C NMR Chemical Shifts

Castro, Sebastián J; García, Manuela E.; Padrón, José M.; Navarro‐Vázquez, Armando; Gil, Roberto R.; Nicotra, Viviana E.

doi:10.1021/acs.jnatprod.8b00162

Cited by 14 publications

(7 citation statements)

References 38 publications

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“…CASE and CASE-3D have been successfully deployed in the structural revision or structure elucidation of natural products. Elyashberg et al [22] reviewed CASE-based structural revision in 2010, and a more recent study involving the use of CASE-3D in the phytochemical study of Senecio volckmannii has been reported by Castro et al in 2018 [29].…”

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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Section: Nmr Spectroscopymentioning

confidence: 99%

Computationally-assisted discovery and structure elucidation of natural products

Nugroho

Morita

2019

J Nat Med

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“…However, two very recent reports have described the development of a different form of CASE program, called StereoFitter, that is specifically designed to determine 3D stereochemistry. [ 135,136 ] The basic idea is similar to that in Reference 4, i.e., using two or more stereospecific parameters in concert to aid in deducing 3D structures. In the published articles to date, RDCs and a comparison of DFT‐calculated and experimental chemical shifts are used.…”

Section: Use Of a Computer‐assisted Structure Elucidation Program (Camentioning

confidence: 99%

Minimizing the risk of deducing wrong natural product structures from NMR data

Burns

Reynolds

2019

Magnetic Reson in Chemistry

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There continues to be a disturbing number of natural products reported in the literature whose structures are incorrect. At least in part, this reflects the fact that many natural product chemists have limited formal nuclear magnetic resonance training. Gaps in training and lack of awareness regarding the challenges and ambiguities associated with two‐dimensional nuclear magnetic resonance data interpretation can easily lead to errors in structure elucidation. The purpose of this tutorial is to point out some of these issues, highlight the kinds of errors that have been made and provide specific advice on how to avoid these missteps such that the risk of reporting a wrong structure is minimized.

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“…The determination of the relative configuration of marine natural products usually follows the constitutional structure elucidation. Despite numerous attempts, there is so far no standard or even automated protocol for the configurational and conformational assignment of natural products or small organic molecules in general [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. Although recently, the application of anisotropic NMR data, such as residual dipolar couplings (RDCs) or residual chemical shift anisotropy (RCSA), has become more and more popular, the cross-relaxation (NOE or ROE) from which interproton distances can be obtained is still a major source of structural information.…”

Section: Introductionmentioning

confidence: 99%

Model-Free Approach for the Configurational Analysis of Marine Natural Products

2021

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The NMR-based configurational analysis of complex marine natural products is still not a routine task. Different NMR parameters are used for the assignment of the relative configuration: NOE/ROE, homo- and heteronuclear J couplings as well as anisotropic parameters. The combined distance geometry (DG) and distance bounds driven dynamics (DDD) method allows a model-free approach for the determination of the relative configuration that is invariant to the choice of an initial starting structure and does not rely on comparisons with (DFT) calculated structures. Here, we will discuss the configurational analysis of five complex marine natural products or synthetic derivatives thereof: the cis-palau’amine derivatives 1a and 1b, tetrabromostyloguanidine (1c), plakilactone H (2), and manzamine A (3). The certainty of configurational assignments is evaluated in view of the accuracy of the NOE/ROE data available. These case studies will show the prospective breadth of application of the DG/DDD method.

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Phytochemical Study of Senecio volckmannii Assisted by CASE-3D with Residual Dipolar Couplings and Isotropic ¹H/¹³C NMR Chemical Shifts

Cited by 14 publications

References 38 publications

Computationally-assisted discovery and structure elucidation of natural products

Computationally-assisted discovery and structure elucidation of natural products

Minimizing the risk of deducing wrong natural product structures from NMR data

Model-Free Approach for the Configurational Analysis of Marine Natural Products

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