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      Recent trends in the structural revision of natural products

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          Abstract

          Case study-based review on misassigned structures and measures to avoid erroneous assignments during structure determination.

          Abstract

          Covering: 2012 to 2017

          This article reviews recent reports on the structural revision of natural products. Through a critical assessment of the original and revised published structures, the article addresses why each structure was targeted for revision, discusses the techniques and key discrepancies that led to the proposal of the revised structure, and offers measures that may have been taken during the original structure determination to prevent error. With the revised structures in hand, weaknesses of original proposals are assessed, providing a better understanding on the logic behind structure determination.

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          Most cited references125

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          Chemistry and biology of siderophores.

          Siderophores are compounds produced by bacteria, fungi and graminaceous plants for scavenging iron from the environment. They are low-molecular-weight compounds (500-1500 daltons) possessing a high affinity for iron(III) (Kf > 1030), the biosynthesis of which is regulated by iron levels and the function of which is to supply iron to the cell. This article briefly describes the classification and chemical properties of siderophores, before outlining research on siderophore biosynthesis and transport. Clinically important siderophores and the therapeutic potential of siderophore design are described. Appendix 1 provides a comprehensive list of siderophore structures.
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            Counting on natural products for drug design.

            Natural products and their molecular frameworks have a long tradition as valuable starting points for medicinal chemistry and drug discovery. Recently, there has been a revitalization of interest in the inclusion of these chemotypes in compound collections for screening and achieving selective target modulation. Here we discuss natural-product-inspired drug discovery with a focus on recent advances in the design of synthetically tractable small molecules that mimic nature's chemistry. We highlight the potential of innovative computational tools in processing structurally complex natural products to predict their macromolecular targets and attempt to forecast the role that natural-product-derived fragments and fragment-like natural products will play in next-generation drug discovery.
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              Computational prediction of 1H and 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry.

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                Author and article information

                Journal
                NPRRDF
                Natural Product Reports
                Nat. Prod. Rep.
                Royal Society of Chemistry (RSC)
                0265-0568
                1460-4752
                2018
                2018
                : 35
                : 6
                : 514-531
                Affiliations
                [1 ]School of Chemistry and Biochemistry
                [2 ]Georgia Institute of Technology
                [3 ]Atlanta
                [4 ]USA
                [5 ]Aquatic Chemical Ecology Center
                [6 ]School of Biological Sciences
                Article
                10.1039/C8NP00011E
                6013367
                29623331
                f466cf8c-34da-42df-bb48-297b7300e97c
                © 2018

                http://rsc.li/journals-terms-of-use

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