ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Interactive Bioconjugation at N-Terminal Cysteines by Using O-Salicylaldehyde Esters towards Dual Site-Selective Functionalization.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Toward Precision Bioconjugation: Chemical Strategies for Site-Selective Cysteine Conjugation.Precision chemistry · 2026Review
- "Lys-Leu" Motif Empowers ExpedientJACS Au · 2026Article
- Article
- Article
- Tunable Heteroaromatic Nitriles for Selective Bioorthogonal Click Reaction with Cysteine.Bioconjugate chemistry · 2023Article
- Interactive Bioconjugation at N-Terminal Cysteines by Using O-Salicylaldehyde Esters towards Dual Site-Selective Functionalization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
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5 authors.
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Abstract
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.
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