Asymmetric Organocatalysis Accelerated via Self‐Assembled Minimal Structures

Sinibaldi, Arianna; Penna, Francesca Della; Ponzetti, Marco; Fini, Francesco; Marchesan, Silvia; Baschieri, Andrea; Pesciaioli, Fabio; Carlone, Armando

doi:10.1002/ejoc.202101042

Cited by 7 publications

(2 citation statements)

References 47 publications

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“…Recently, an emerging topic regarded self-assembled short peptides acting as organocatalysts. Their efficiencies are comparable to those found in enzymes [23,24], and their supramolecular state can accelerate the organocatalysis activity [25][26][27].…”

Section: Introductionmentioning

confidence: 57%

Peptidomimetic-Based Asymmetric Catalysts

2023

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Despite the great advantages of peptidomimetic scaffolds, there are only a few examples of their application in the field of asymmetric catalysis. Peptidomimetic scaffolds offer numerous advantages related to their easy preparation, modular and tunable structures, and biomimetic features, which make them well suited as chiral catalysts. This review underlines the structure–function relationship for catalytic properties towards efficient enantioselective catalysis.

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Section: Introductionmentioning

confidence: 57%

Peptidomimetic-Based Asymmetric Catalysts

2023

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“…[15][16][17] In this respect, prior studies combined catalysis with other 'life-like' features such as replication, [18][19][20] dissipative self-assembly, [21][22][23][24][25] or the formation of dynamic and responsive soft materials. [26][27][28] Although there are examples of enhancement of activity of organocatalysts through formation of supramolecular assemblies, 29 there is little knowledge of how specific interactions within the assemblies affect their catalytic properties. As a consequence, tuning the activity and stereoselectivity of supramolecular catalysts is far from trivial.…”

Section: Introductionmentioning

confidence: 99%

Modifying the Catalytic Activity of Lipopeptide Assemblies with Nucleobases

Vela‐Gallego,

Lewandowski,

Möhler

et al. 2023

Chemistry A European J

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Biohybrid catalysts that operate in aqueous media are intriguing for systems chemistry. In this paper, we investigate whether control over the self‐assembly of biohybrid catalysts can tune their properties. As a model, we use the catalytic activity of functional hybrid molecules consisting of a catalytic H‐dPro‐Pro‐Glu tripeptide, derivatized with fatty acid and nucleobase moieties. This combination of simple biological components merged the catalytic properties of the peptide with the self‐assembly of the lipid, and the structural ordering of the nucleobases. The biomolecule hybrids self‐assemble in aqueous media into fibrillar assemblies and catalyze the reaction between butanal and nitrostyrene. The interactions between the nucleobases enhanced the order of the supramolecular structures and affected their catalytic activity and stereoselectivity. The results point to the significant control and ordering that nucleobases can provide in the self‐assembly of biologically inspired supramolecular catalysts.

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Stereoselective Reactions Promoted by Alkali Metal Salts of Phosphoric Acid Organocatalysts

Cocco,

Antenucci,

Carlone

et al. 2024

ChemCatChem

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The catalytic application of chiral phosphoric acids (CPAs) from 2004 to date represents a true milestone for asymmetric organocatalysis. However, not only the free acids can be conveniently employed in numerous different asymmetric synthetic methodologies, thus being strictly compliant to the concept of “organocatalysis”, but also their metal salts. This review focuses on asymmetric reactions in which the catalyst is a chiral alkali or alkaline‐earth metal phosphate.

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Asymmetric Organocatalysis Accelerated via Self‐Assembled Minimal Structures

Abstract: Part of the "Organocatalysis" Special Collection.

Cited by 7 publications

References 47 publications

Peptidomimetic-Based Asymmetric Catalysts

Peptidomimetic-Based Asymmetric Catalysts

Modifying the Catalytic Activity of Lipopeptide Assemblies with Nucleobases

Stereoselective Reactions Promoted by Alkali Metal Salts of Phosphoric Acid Organocatalysts

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