Comment on “Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence”

Sherman, David H.; Tsukamoto, Sachiko; Williams, Robert M.

doi:10.1126/science.aaa9349

Cited by 7 publications

(12 citation statements)

References 14 publications

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“…Secondly, four compounds are partial racemates, which (if the above is true) suggests these compounds are biosynthesized via two routes in non-equivalent amounts. This type of enantiodivergent biosynthesis has previously been observed in related bromotyrosine and bromopyrrole alkaloids [3,[23][24][25]. While it is possible that this chiral center could undergo epimerization during handling, this is unlikely as partial racemization was seen in only four out of the seven compounds isolated from the same extract, and all compounds were handled identically.…”

Section: Resultssupporting

confidence: 62%

Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata

2019

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Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as natural products—lamellomorphamides A (3), B (4), C (5) and D (6). In addition, fifteen previously reported natural products were isolated, seven of which are seco analogs of hamacanthin alkaloids. The one sponge produces enantiomerically pure but opposite configurations of compounds that only differ in the number of bromines, suggesting enantiodivergent biosynthesis. In addition, four compounds were isolated as partial racemates, suggesting these compounds are biosynthesized via two independent routes.

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Section: Resultssupporting

confidence: 62%

Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata

2019

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“…The origin of life is about chirality because of its existence in biomolecules, such as nucleic acids, proteins, and carbohydrates and its involving in biological mechanism in human beings, animals, and plants on the earth [1][2][3][4][5][6]. Chirality has also become increasingly important in pharmaceutical science and industry on the design, discovery, and development of drugs for enhancing their potency and selectivity [5,6].…”

Section: Introductionmentioning

confidence: 99%

Multilayer 3D Chirality and Its Synthetic Assembly

Liu

Yang

et al. 2019

Research

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3D chirality of sandwich type of organic molecules has been discovered. The key element of this chirality is characterized by three layers of structures that are arranged nearly in parallel fashion with one on top and one down from the center plane. Individual enantiomers of these molecules have been fully characterized by spectroscopies with their enantiomeric purity measured by chiral HPLC. The absolute configuration was unambiguously assigned by X-ray diffraction analysis. This is the first multilayer 3D chirality reported and is anticipated to lead to a new research area of asymmetric synthesis and catalysis and to have a broad impact on chemical, medicinal, and material sciences in future.

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“…Although rare, there are nevertheless instances where either both enantiomers occur or enantiomeric congeners of opposite antipodal series are produced. These enantiomeric natural products have been found from a variety of sources, including plants, microbes, marine and terrestrial organisms, etc., and include examples from various natural product compound classes such as terpenes, phenylpropanoids, polyketides, and alkaloids. , They can be found from the same species as either a racemic or scalemic mixture or from different species (where one enantiomer occurs in one species and the other enantiomer occurs in another species). In the case of the plant monoterpenoid indole alkaloids, most of the enantiomeric metabolites occur in different species as a single enantiomer and only sometimes as a racemic mixture.…”

mentioning

confidence: 99%

Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

et al. 2017

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Reexamination of the absolute configuration of recently isolated eburnane alkaloids from Malaysian Kopsia and Leuconotis species by X-ray diffraction analysis and ECD/TDDFT has revealed the existence of biosynthetic enantiodivergence. Three different scenarios are discerned with respect to the composition of the enantiomeric eburnane alkaloids in these plants: first, where the new eburnane congeners possess the same C-20, C-21 absolute configurations as the common eburnane alkaloids (eburnamonine, eburnamine, isoeburnamine, eburnamenine) occurring in the same plant; second, where the new eburnane congeners possess opposite or enantiomeric C-20, C-21 absolute configurations compared to the common eburnane alkaloids found in the same plant; and, third, where the four common eburnane alkaloids were isolated as racemic or scalemic mixtures, while the new eburnane congeners were isolated as pure enantiomers with a common C-20, C-21 configuration (20α, 21α). Additionally, the same Kopsia species (K. pauciflora) found in two different geographical locations (Peninsular Malaysia and Malaysian Borneo) showed different patterns in the composition of the enantiomeric eburnane alkaloids. Revision of the absolute configurations of a number of new eburnane congeners (previously assigned based on the assumption of a common biogenetic origin to that of the known eburnane alkaloids co-occurring in the same plant) is required based on the present results.

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Comment on “Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence”

Cited by 7 publications

References 14 publications

Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata

Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata

Multilayer 3D Chirality and Its Synthetic Assembly

Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

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