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Orthogonally Stimulated Assembly/Disassembly of Depsipeptides by Rational Chemical Design.


ABSTRACT: Controlling the assembly and disassembly of cross-β-sheet-forming peptides is one of the predominant challenges for this class of supramolecular material. As they constitute a continuously propagating material, every atomic change can be exploited to bring about distinct responses at the architectural level. We report herein that, by using rational chemical design, serine and methionine can both be used as orthogonal chemical triggers to signal assembly/disassembly through their corresponding stimuli. Serine is used to construct an ester-bond oligopeptide that can undergo O,N-acyl rearrangement, whereas methionine is sensitive to oxidation by H2 O2 . Using the example peptide sequence, KIKISQINM, we demonstrate that assembly and disassembly can be independently controlled on demand.

SUBMITTER: Pieszka M 

PROVIDER: S-EPMC6593846 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Orthogonally Stimulated Assembly/Disassembly of Depsipeptides by Rational Chemical Design.

Pieszka Michaela M   Sobota Adriana Maria AM   Gačanin Jasmina J   Weil Tanja T   Ng David Y W DYW  

Chembiochem : a European journal of chemical biology 20190412 11


Controlling the assembly and disassembly of cross-β-sheet-forming peptides is one of the predominant challenges for this class of supramolecular material. As they constitute a continuously propagating material, every atomic change can be exploited to bring about distinct responses at the architectural level. We report herein that, by using rational chemical design, serine and methionine can both be used as orthogonal chemical triggers to signal assembly/disassembly through their corresponding st  ...[more]

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