Hydrolase–like catalysis and structural resolution of natural products by a metal–organic framework

Mon, Marta; Bruno, Rosaria; Sanz-Navarro, Sergio; Negro, Cristina; Ferrando-Soria, Jesús; Bartella, Lucia; Donna, Leonardo Di; Prejanò, Mario; Marino, Tiziana; Leyva‐Pérez, Antonio; Armentano, Donatella; Pardo, Emilio

doi:10.1038/s41467-020-16699-3

Cited by 41 publications

(32 citation statements)

References 50 publications

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“…[8][9][10][11][12] Indeed, the rational use of such interaction for specific applications has been barely explored. [13][14][15][16][17][18][19][20] Metal-organic frameworks (MOFs) [21][22][23][24][25][26][27][28] are a class of crystalline porous inorganic-organic materials, whose rich host-guest chemistry [29][30][31][32][33][34][35] and high crystallinity, [36][37][38] together with the possibility to have -to a certain extent-a control of their dimensionality, topology and functionality by chemical design, [39][40][41][42][43][44][45] have situate them in an advantageous position with respect to other porous materials. This has been clearly exemplified by the continuous growth of novel aesthetically pleasant crystal structures, [46][47][48][49] as well as by the wide range of applications where they have shown successful, for example gas storage and separation, catalysis, drug delivery, conductivity, molecular recognition of small molecules, encapsulation of functional moieties, magnetism, chemical nanoreactors and water remediation.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Organic Frameworks as Unique Platforms to Gain Insight of σ‐Hole Interactions for the Removal of Organic Dyes from Aquatic Ecosystems

Negro

Escamilla

Bruno

et al. 2022

Chemistry A European J

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The combination of high crystallinity and rich hostguest chemistry in metal-organic frameworks (MOFs), have situated them in an advantageous position, with respect to traditional porous materials, to gain insight on specific weak noncovalent supramolecular interactions. In particular, sulfur σ-hole interactions are known to play a key role in the biological activity of living beings as well as on relevant molecular recognitions processes. However, so far, they have been barely explored. Here, we describe both how the combination of the intrinsic features of MOFs, especially the possibility of using single-crystal X-ray crystallography (SCXRD), can be an extremely valuable tool to gain insight on sulfur σ-hole interactions, and how their rational exploitation can be enormously useful in the efficient removal of harmful organic molecules from aquatic ecosystems. Thus, we have used a MOF, prepared from the amino acid L-methionine and possessing channels decorated with À CH 2 CH 2 SCH 3 thioalkyl chains, to remove a family of organic dyes at very low concentrations (10 ppm) from water. This MOF is able to efficiently capture the four dyes in a very fast manner, reaching within five minutes nearly the maximum removal. Remarkably, the crystal structure of the different organic dyes within MOFs channels could be determined by SCXRD. This has enabled us to directly visualize the important role sulfur σ-hole interactions play on the removal of organic dyes from aqueous solutions, representing one of the first studies on the rational exploitation of σ-hole interactions for water remediation.

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Section: Introductionmentioning

confidence: 99%

Metal‐Organic Frameworks as Unique Platforms to Gain Insight of σ‐Hole Interactions for the Removal of Organic Dyes from Aquatic Ecosystems

Negro

Escamilla

Bruno

et al. 2022

Chemistry A European J

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“…The increasing improvement and availability of modern analytical techniques including MS, NMR, X-ray crystallography, and electron microscopy have revolutionized structural elucidation. Recently, the extended versions of crystallography such as crystalline sponges, cocrystallizations, and encapsulated frameworks and electron diffraction techniques have made outstanding contributions to the analysis of configuration. However, studies of the compounds for which the sizes are mismatched with the sizes of hosts or noncrystallizable flexible complex molecules are still challenging, and the determination of absolute configuration remains a formidable task.…”

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confidence: 99%

Structural Elucidation of Garcipaucinones A and B From Garcinia paucinervis Using Quantum Chemical Calculations

et al. 2021

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Two tocotrienol derivatives, garcipaucinones A (1) and B (2), and a biosynthetically related known analogue (3) were isolated from the fruit of Garcinia paucinervis. Their structures including absolute configurations were unequivocally determined by spectroscopic methods complemented with electronic circular dichroism (ECD) calculations and gauge-independent atomic orbital (GIAO) NMR calculations. Compounds 1 and 2 are the first naturally occurring tocotrienol derivatives with a 3,10-dioxatricyclo-[7.3.1.02,7]tridecane skeleton incorporating an unusual γ-pyrone motif. A reasonable biosynthetic pathway for formation of the two compounds is proposed. The antiproliferative and anti-inflammatory activities of compounds 1 and 2 were also evaluated.

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“…Hierarchical self-assembly with long-range spatial arrangement is ubiquitous in nature and is of widespread interest for engineering materials with enhanced properties (1)(2)(3)(4)(5) for applications in photonics (6), energy storage (7), drug delivery (8), gas adsorption (9), and catalysis (10). For example, hierarchical self-assembly via multiple noninterfering interactions on different length scales in a spatiotemporally controlled manner is the basis of various essential biological superstructures, such as supercoiled DNA (11), folded proteins (12), and biologically active cell membranes (13).…”

Section: Introductionmentioning

confidence: 99%

Superstructured mesocrystals through multiple inherent molecular interactions for highly reversible sodium ion batteries

Qiu

Wang

et al. 2021

Sci. Adv.

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Soft structures in nature, such as supercoiled DNA and proteins, can organize into complex hierarchical architectures through multiple noncovalent molecular interactions. Identifying new classes of natural building blocks capable of facilitating long-range hierarchical structuring has remained an elusive goal. We report the bottom-up synthesis of a hierarchical metal-phenolic mesocrystal where self-assembly proceeds on different length scales in a spatiotemporally controlled manner. Phenolic-based coordination complexes organize into supramolecular threads that assemble into tertiary nanoscale filaments, lastly packing into quaternary mesocrystals. The hierarchically ordered structures are preserved after thermal conversion into a metal-carbon hybrid framework and can impart outstanding performance to sodium ion batteries, which affords a capability of 72.5 milliampere hours per gram at an ultrahigh rate of 200 amperes per gram and a 90% capacity retention over 15,000 cycles at a current density of 5.0 amperes per gram. This hierarchical structuring of natural polyphenols is expected to find widespread applications.

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Hydrolase–like catalysis and structural resolution of natural products by a metal–organic framework

Cited by 41 publications

References 50 publications

Metal‐Organic Frameworks as Unique Platforms to Gain Insight of σ‐Hole Interactions for the Removal of Organic Dyes from Aquatic Ecosystems

Metal‐Organic Frameworks as Unique Platforms to Gain Insight of σ‐Hole Interactions for the Removal of Organic Dyes from Aquatic Ecosystems

Structural Elucidation of Garcipaucinones A and B From Garcinia paucinervis Using Quantum Chemical Calculations

Superstructured mesocrystals through multiple inherent molecular interactions for highly reversible sodium ion batteries

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