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Orthogonally Stimulated Assembly/Disassembly of Depsipeptides by Rational Chemical Design
Author(s) -
Pieszka Michaela,
Sobota Adriana Maria,
Gačanin Jasmina,
Weil Tanja,
Ng David Y. W.
Publication year - 2019
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800781
Subject(s) - rational design , oligopeptide , serine , supramolecular chemistry , chemistry , methionine , sequence (biology) , peptide , construct (python library) , combinatorial chemistry , nanotechnology , stereochemistry , amino acid , computer science , biochemistry , molecule , materials science , enzyme , organic chemistry , programming language
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 H 2 O 2 . Using the example peptide sequence, KIKISQINM, we demonstrate that assembly and disassembly can be independently controlled on demand.