Boc-Cys(Acm)-ONp contains a cysteine-derived amino acid framework bearing an N-terminal Boc (tert-butoxycarbonyl) protecting group and a Cys side chain substituted with an Acm (acetamidomethyl) thioether-protecting group, with the carboxyl group converted to an ONp (p-nitrophenyl) ester. The molecule presents both an N-protected amino functionality and a masked carboxyl group as a reactive p-nitrophenyl ester, while the Acm group controls the thiol reactivity of the cysteine side chain and the Boc group limits amine participation in side reactions during handling and coupling. Boc-Cys(Acm)-ONp is used as a peptide-synthesis building block or intermediate in stepwise formation of amide linkages, where the orthogonal protection pattern supports chemoselective transformations and downstream conversion to cysteine-containing peptide derivatives.
CAT No: CP00624
CAS No:58651-76-6
Synonyms/Alias:Boc-S-acetamidomethyl-L-cysteine 4-nitrophenyl ester;
Boc-Cys(Acm)-ONp is a protected cysteine derivative featuring an N-terminal Boc group, a side-chain Acm thioether-protected cysteine motif, and an ONp ester at the C-terminus for activated segment coupling. This reagent is widely used in peptide synthesis workflows where controlled cysteine chemistry is required, enabling later selective cysteine deprotection and chemoselective transformations while minimizing side reactions during chain assembly. The presence of the activated ONp ester supports efficient formation of peptide bonds under standard coupling conditions used for protected amino acid building blocks.
1. Peptide Segment Coupling
Boc-Cys(Acm)-ONp is commonly used by peptide synthesis groups to prepare cysteine-containing peptide segments with an activated C-terminus, supporting efficient amide bond formation during solution-phase or mixed coupling strategies. The Boc group provides N-terminal protection for compatibility with protected-amino-acid assembly, while the Acm protection on the thiol is chosen to suppress premature disulfide formation and side reactions during iterative chain elongation. Researchers developing cysteine-rich peptides, including those intended for subsequent thiol-directed modifications, often select this specific protection pattern to maintain cysteine integrity through the coupling and purification steps of intermediate peptide construction.
2. Disulfide-Controlled Peptide Synthesis
Boc-Cys(Acm)-ONp is frequently selected for building peptides where disulfide topology is introduced late in the synthesis sequence. The Acm-protected cysteine side chain helps prevent uncontrolled oxidation during synthesis and handling, allowing the final disulfide-forming step to be performed after the peptide backbone is assembled and purified. Peptide chemists and custom peptide manufacturing teams use this reagent to generate intermediates that can be converted into defined cystine motifs under controlled conditions, which is particularly valuable for peptides requiring specific intramolecular or intermolecular disulfide patterns for downstream chemical biology studies.
3. Late-Stage Cysteine Functionalization
Boc-Cys(Acm)-ONp is used as a cysteine-incorporating building block for workflows that require late-stage thiol availability for conjugation or labeling chemistry. After peptide assembly, the Acm-protected cysteine can be unmasked to provide a reactive thiol handle for selective coupling to electrophiles or for site-selective attachment strategies that rely on cysteine chemistry rather than backbone modification. This makes the reagent a practical choice for teams preparing functional peptide conjugates, such as peptide-based probes, affinity reagents, or chemically modified peptide standards, where controlling the timing of thiol generation improves reproducibility and reduces undesired side reactions.
4. Pharmaceutical Intermediate Peptide Fragments
Boc-Cys(Acm)-ONp is also applied in the development of protected peptide fragments used as intermediates in medicinal chemistry and peptide-drug discovery programs. Synthetic chemistry teams use this building block to introduce a cysteine residue with a protection scheme that supports downstream elaboration while maintaining stability during fragment assembly and intermediate purification. The ONp activation and orthogonal cysteine protection pattern help streamline the preparation of defined peptide fragments that can later be carried into further synthetic steps, including selective cysteine transformations required for final candidate synthesis and analytical characterization.
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