6533b874fe1ef96bd12d636c

RESEARCH PRODUCT

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

Emilio PardoDonatella ArmentanoAntonio Leyva-pérezMarta MonRosaria BrunoJesús Ferrando-soriaSergio Sanz-navarroTiziana MarinoLeonardo Di DonnaCristina NegroLucia BartellaMario Prejanò

subject

Multidisciplinary010405 organic chemistryChemistryChemical structureScienceQSupramolecular chemistryAbsolute configurationGeneral Physics and AstronomyTotal synthesisGeneral ChemistryMetal-organic frameworks010402 general chemistry01 natural sciencesCombinatorial chemistryGeneral Biochemistry Genetics and Molecular BiologyArticle0104 chemical sciencesCatalysisHydrolysisHydrolaseBiocatalysisMoleculelcsh:Qlcsh:Science

description

[EN] The exact chemical structure of non-crystallising natural products is still one of the main challenges in Natural Sciences. Despite tremendous advances in total synthesis, the absolute structural determination of a myriad of natural products with very sensitive chemical functionalities remains undone. Here, we show that a metal-organic framework (MOF) with alcohol-containing arms and adsorbed water, enables selective hydrolysis of glycosyl bonds, supramolecular order with the so-formed chiral fragments and absolute determination of the organic structure by single-crystal X-ray crystallography in a single operation. This combined strategy based on a biomimetic, cheap, robust and multigram available solid catalyst opens the door to determine the absolute configuration of ketal compounds regardless degradation sensitiveness, and also to design extremely-mild metal-free solid-catalysed processes without formal acid protons. Elucidation of the chemical structure of natural products constitutes one of the main challenges in Natural Sciences. Here, the authors show that an amino acid-based metal-organic framework exhibits hydrolase-like catalytic activity and crystallographic determination of the resulting products

10.1038/s41467-020-16699-3http://dx.doi.org/10.1038/s41467-020-16699-3