Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt is a Boc-protected L-cysteine derivative in which the thiol side chain is converted to an S-allyloxy (thioether/allyl-protected) functionality and the carboxyl group is present as an amidomethyl-type protected form. The molecule bears a tert-butoxycarbonyl (Boc) group on the amino functionality, an allyloxy substituent on sulfur that can be removed under appropriate deprotection conditions, and a dicyclohexylamine counterion associated with the salt form, while retaining the amino and carboxyl-derived functionality required for peptide-building chemistry. In peptide synthesis workflows, the combination of Boc protection and sulfur side-chain protection supports stepwise coupling by reducing undesired side reactions from the cysteine thiol and by providing a controlled handle for later conversion to a cysteine-like functionality for conjugation, crosslinking, or structure-activity studies.
CAT No: CP00620
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt is an L-cysteine-derived, N-Boc protected amino acid derivative in which the thiol is converted to an S-allyloxy thioether and the side-chain is further functionalized through an amidomethyl handle. The molecule contains a stereogenic center at the α-carbon, a carbamate-protected amine (Boc), an allyloxy sulfur substituent that can be cleanly manipulated under thiol-protection and deprotection chemistries, and a cationic amidomethyl amide motif paired with dicyclohexylamine as a salt-forming counterion. The presence of the Boc group and the thioether/allyl functionality supports orthogonal protection logic for peptide coupling, while the amidomethyl functionality can participate in downstream transformations toward amide and thioether-containing scaffolds. The salt form can improve handling and solubility in peptide synthesis workflows and related fine chemical operations, making the compound a practical chiral intermediate for cysteine chemistry.
1. Peptide Synthesis
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt supports peptide building block preparation and cysteine-site incorporation in solid-phase or solution-phase assembly strategies. The Boc-protected N-terminus and the S-allyloxy thioether provide side-chain protection compatible with peptide coupling conditions, while the L-configuration at the α-carbon maintains stereochemical fidelity during amide bond formation. The amidomethyl functionality can be used to construct defined linkages or to enable controlled side-chain elaboration after coupling, including orthogonal deprotection sequences that reveal reactive cysteine-like functionality. Downstream, the resulting cysteine-containing peptides and peptide fragments can be used for mapping disulfide patterns, preparing thioether-stabilized analogs, and generating peptide libraries that require consistent stereochemistry and protected sulfur chemistry.
2. Side-Chain Functionalization
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt is well suited to side-chain functionalization workflows that exploit the protected sulfur and the allyl group for controlled chemical editing. The S-allyloxy substituent can serve as an orthogonal protection platform for sulfur chemistry, enabling selective transformations that convert between protected and reactive sulfur states without disturbing the Boc carbamate during early-stage steps. The amidomethyl motif can participate in constructing additional amide linkages or serve as a handle for further derivatization toward constrained linkers and cysteine-mimetic motifs. Resulting derivatives can feed into peptidomimetic construction, linker engineering for conjugates, and synthetic intermediate preparation where sulfur-containing functional groups must be introduced with stereochemical control.
3. Bioconjugation Chemistry
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt can be applied in bioconjugation chemistry where cysteine-derived attachment points and sulfur-reactive sites are required for controlled coupling to biomolecules. The compound's protected amine and protected sulfur chemistry allow it to be carried through synthesis steps while minimizing unwanted side reactions, and the L-cysteine backbone supports predictable spatial orientation of the sulfur-containing functionality. The allyloxy-protected sulfur and amidomethyl functionality can be leveraged to generate conjugation-ready intermediates that later undergo deprotection or functional group conversion to install thiol-reactive or thioether-stabilized linkages. Downstream products include cysteine-functional peptide conjugates, protein labeling reagents, and linker-bearing biomolecule fragments that align with amino acid derivatization and peptide science workflows.
4. Peptidomimetics And SAR Studies
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt is suitable for peptidomimetic and structure-activity relationship studies that require cysteine-position control within constrained scaffolds. The α-amino acid stereochemistry and Boc protection support incorporation into analogs where amide connectivity must be defined, while the S-allyloxy sulfur protection allows systematic variation of sulfur oxidation state or substitution pattern after scaffold assembly. The amidomethyl handle can be used to tune linker length, introduce additional amide constraints, or enable conversion into alternative side-chain architectures that mimic cysteine reactivity profiles. Resulting analog series can be used to interrogate how side-chain sulfur chemistry and stereochemical placement influence molecular recognition, supporting SAR-oriented synthesis of cysteine-containing peptide mimics.
5. Pharmaceutical Intermediate Preparation
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt functions as a chiral amino acid intermediate for pharmaceutical intermediate preparation and fine chemical synthesis routes that require protected cysteine functionality. The Boc carbamate provides a robust N-protection state for controlled coupling chemistry, while the allyloxy sulfur substituent can be carried through multi-step sequences and later converted to desired sulfur-containing motifs used in active pharmaceutical ingredient (API) intermediate scaffolds. The salt-forming dicyclohexylamine can support practical isolation and handling in manufacturing-oriented workflows where consistent physical properties matter for downstream processing. Downstream utility includes generation of protected cysteine derivatives, linker building blocks, and stereodefined intermediates that integrate into larger synthetic schemes for medicinal chemistry and process chemistry development.
6. Process Chemistry Intermediate
Boc-S-allyloxy-amidomethyl-L-cysteine dicyclohexylamine salt is applicable to process chemistry intermediate preparation where orthogonal protection and predictable functional group reactivity support scalable synthetic planning. The combination of Boc protection on the amino group, S-allyloxy sulfur protection, and the amidomethyl amide functionality enables stepwise transformations with reduced risk of cross-reactivity across functional groups. The compound's defined L-stereochemistry supports reproducible chiral outcomes for downstream coupling and derivatization steps, aligning with chiral building block requirements in industrial amino acid derivative manufacturing. Resulting intermediates can be employed to produce protected cysteine-containing fragments, sulfur-functional linkers, and peptide-compatible building blocks used in specialty chemical production and industrial chemical manufacturing pipelines.
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