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Interactive Bioconjugation at N‐Terminal Cysteines by Using O‐Salicylaldehyde Esters towards Dual Site‐Selective Functionalization

Silva, Maria J. S. A. ; Cavadas, Rafaela A. N. ; Faustino, Hélio ; Veiros, Luís F. ; Gois, Pedro M. P.

Chemistry : a European journal, 2022-12, Vol.28 (67), p.e202202377-n/a [Periódico revisado por pares]

Germany: Wiley Subscription Services, Inc

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  • Título:
    Interactive Bioconjugation at N‐Terminal Cysteines by Using O‐Salicylaldehyde Esters towards Dual Site‐Selective Functionalization
  • Autor: Silva, Maria J. S. A. ; Cavadas, Rafaela A. N. ; Faustino, Hélio ; Veiros, Luís F. ; Gois, Pedro M. P.
  • Assuntos: Aldehydes ; bioconjugation ; Chemistry ; Conjugates ; Conjugation ; Cysteine - chemistry ; Esters ; Esters - chemistry ; irreversible deconjugation ; N-terminal cysteine ; Phenolic compounds ; Phenols ; protecting group ; Reagents ; Thiazolidines
  • É parte de: Chemistry : a European journal, 2022-12, Vol.28 (67), p.e202202377-n/a
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: N‐terminal Cys modification has been intensively studied to produce homogeneous bioconjugates essentially through two modes of reaction: reversible modification with the equilibrium shifted towards the formation of the desired conjugate or stable and irreversible conjugates. Herein, we report a new method of N‐terminal cysteine modification using O‐salicylaldehyde esters (OSAEs) through fast conjugation and irreversible deconjugation. These reagents can rapidly react with N‐terminal Cys at low‐micromolar concentration to form thiazolidines with subsequent hydrolysis of the ester moiety to the phenolic derivative. These phenolic thiazolidines can be hydrolyzed at acidic pH (≈4.5) to recover the intact N‐terminal Cys. Bioconjugation reactions using OSAEs offer controlled reversibility to as act as a protecting group for N‐terminal cysteines, allowing the modification of in‐chain residues without perturbing the N‐terminal Cys, which can then be deprotected and used as a conjugation site. Two‐way protection: O‐Salicylaldehyde esters are suitable handles for the site‐specific protection of N‐terminal cysteines on native peptides. The resulting phenolic thiazolidines present tunable stability through careful pH control that allows the orthogonal multifunctionalization of different Cys residues driven by interactive site‐selective peptide modifications.
  • Editor: Germany: Wiley Subscription Services, Inc
  • Idioma: Inglês
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