Acylphosphates as versatile transient species in reaction networks and optical catalyst screenings

Englert, Andreas; Majer, Felix; Schiessl, Jannik L.; Kuehne, Alexander J.C.; von Delius, Max

doi:10.1016/j.chempr.2023.11.015

Chem

2024

DOI: 10.1016/j.chempr.2023.11.015

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Acylphosphates as versatile transient species in reaction networks and optical catalyst screenings

Andreas Englert,

Felix Majer,

Jannik L. Schiessl

et al.

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2024

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Cited by 4 publications

References 80 publications

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Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels

Pol,

Dai,

Thomann

et al. 2024

Angewandte Chemie

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Despite great progress on the construction of non‐equilibrium systems, most approaches do not consider the structure of the fuel as a critical element to control the processes. Herein, we show that the amino acid side chains (A, F, Nal) in the structure of abiotic phosphates can direct assembly and reactivity during transient structure formation. The fuels bind covalently to substrates and subsequently influence the structures in the assembly process. We focus on the ways in which the phosphate esters guide structure formation and how structures and reactivity cross regulate when constructing assemblies. Through the chemical functionalization of energy‐rich aminoacyl phosphate esters, we are able to control the yield to esters and thioesters upon adding dipeptides containing tyrosine or cysteine residues. The structural elements around the phosphate esters guide the lifetime of the structures formed and their supramolecular assemblies. These properties can further be influenced by the peptide sequence of substrates, incorporating anionic, aliphatic and aromatic residues. Furthermore, we illustrate that oligomerization of esters can be initiated from a single aminoacyl phosphate ester incorporating a tyrosine residue (Y). These findings suggest that activated amino acids with varying reactivity and energy contents can pave the way for designing and fabricating structured fuels.

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Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels

Pol,

Dai,

Thomann

et al. 2024

Angewandte Chemie

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Acyl Phosphates as Chemically Fueled Building Blocks for Self‐Sustaining Protocells

Zozulia,

Kriebisch,

Kriebisch

et al. 2024

Angewandte Chemie

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Lipids spontaneously assemble into vesicle‐forming membranes. Such vesicles serve as compartments for even the simplest living systems. Vesicles have been extensively studied for constructing synthetic cells or as models for protocells—the cells hypothesized to have existed before life. These compartments exist almost always close to equilibrium. Life, however, exists out of equilibrium. In this work, we studied vesicle‐based compartments regulated by a non‐equilibrium chemical reaction network that converts activating agents. In this way, the compartments require a constant or periodic supply of activating agents to sustain themselves. Specifically, we use activating agents to condense carboxylates and phosphate esters into acyl phosphate‐based lipids that form vesicles. These vesicles can only be sustained when condensing agents are present; without them, they decay. We demonstrate that the chemical reaction network can operate on prebiotic activating agents, opening the door to prebiotically plausible, self‐sustainable protocells that compete for resources. In future work, such protocells should be endowed with a genotype, e.g., self‐replicating RNA structures, to alter the protocell's behavior. Such protocells could enable Darwinian evolution in a prebiotically plausible chemical system.

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Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels

Pol,

Dai,

Thomann

et al. 2024

Angew Chem Int Ed

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Acylphosphates as versatile transient species in reaction networks and optical catalyst screenings

Cited by 4 publications

References 80 publications

Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels

Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels

Acyl Phosphates as Chemically Fueled Building Blocks for Self‐Sustaining Protocells

Guiding Transient Peptide Assemblies with Structural Elements Embedded in Abiotic Phosphate Fuels

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