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Spontaneous and Selective Peptide Elongation in Water Driven by Aminoacyl Phosphate Esters and Phase Changes.
Dai, Kun; Pol, Mahesh D; Saile, Lenard; Sharma, Arti; Liu, Bin; Thomann, Ralf; Trefs, Johanna L; Qiu, Danye; Moser, Sandra; Wiesler, Stefan; Balzer, Bizan N; Hugel, Thorsten; Jessen, Henning J; Pappas, Charalampos G.
Afiliação
  • Dai K; DFG Cluster of Excellence livMatS @FIT─Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Pol MD; DFG Cluster of Excellence livMatS @FIT─Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Saile L; DFG Cluster of Excellence livMatS @FIT─Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Sharma A; Freiburg Center for Interactive Materials and Bioinspired Technologies (FIT), University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Liu B; College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002, China.
  • Thomann R; Freiburg Center for Interactive Materials and Bioinspired Technologies (FIT), University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Trefs JL; Freiburg Materials Research Center (FMF), University of Freiburg, Stefan-Meier-Strasse 21, 79104 Freiburg, Germany.
  • Qiu D; DFG Cluster of Excellence livMatS @FIT─Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Moser S; Institute of Physical Chemistry, University of Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.
  • Wiesler S; Institute of Organic Chemistry, University of Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.
  • Balzer BN; Institute of Organic Chemistry, University of Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.
  • Hugel T; Institute of Organic Chemistry, University of Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.
  • Jessen HJ; DFG Cluster of Excellence livMatS @FIT─Freiburg Center for Interactive Materials and Bioinspired Technologies, University of Freiburg, Georges-Köhler-Allee 105, 79110 Freiburg, Germany.
  • Pappas CG; Freiburg Materials Research Center (FMF), University of Freiburg, Stefan-Meier-Strasse 21, 79104 Freiburg, Germany.
J Am Chem Soc ; 145(48): 26086-26094, 2023 12 06.
Article em En | MEDLINE | ID: mdl-37992133
ABSTRACT
Nature chose phosphates to activate amino acids, where reactive intermediates and complex machinery drive the construction of polyamides. Outside of biology, the pathways and mechanisms that allow spontaneous and selective peptide elongation in aqueous abiotic systems remain unclear. Herein we work to uncover those pathways by following the systems chemistry of aminoacyl phosphate esters, synthetic counterparts of aminoacyl adenylates. The phosphate esters act as solubility tags, making hydrophobic amino acids and their oligomers soluble in water and enabling selective elongation and different pathways to emerge. Thus, oligomers up to dodecamers were synthesized in one flask and on the minute time scale, where consecutive additions activated autonomous phase changes. Depending on the pathway, the resulting phases initially carry nonpolar peptides and amphiphilic oligomers containing phosphate esters. During elongation and phosphate release, shorter oligomers dominate in solution, while the aggregated phase favors the presence of longer oligomers due to their self-assembly propensity. Furthermore we demonstrated that the solution phases can be isolated and act as a new environment for continuous elongation, by adding various phosphate esters. These findings suggest that the systems chemistry of aminoacyl phosphate esters can activate a selection mechanism for peptide bond formation by merging aqueous synthesis and self-assembly.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos / Água Idioma: En Revista: J Am Chem Soc Ano de publicação: 2023 Tipo de documento: Article País de afiliação: Alemanha

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Peptídeos / Água Idioma: En Revista: J Am Chem Soc Ano de publicação: 2023 Tipo de documento: Article País de afiliação: Alemanha