(Boc)2-4-cis-GCHC-OH is a protected, non-proteinogenic amino acid derivative featuring a 4-cis substituted side chain and bearing two Boc (tert-butoxycarbonyl) protecting groups on the amino acid framework, along with a free carboxylic acid (-COOH). The molecule contains protected amine functionality that is masked as carbamates, which reduces undesired side reactions during handling and supports chemoselective transformations, while the cis relationship in the side chain defines its stereochemical geometry as specified by the name. In peptide and amino acid derivative synthesis, the Boc-protected amino functionality and carboxyl group enable stepwise assembly of more complex structures and provide a protected intermediate suitable for generating defined, stereochemically constrained amino acid building blocks for chemical biology and structure-activity studies.
CAT No: CP25249
CAS No:126045-22-2
Synonyms/Alias:4-cis-[(Boc)2-guanidino]cyclohexane carboxylic acid
Chemical Name:4-cis-[Bis(t-butyloxycarbonyl)-guanidino]cyclohexane carboxylic acid
(Boc)2-4-cis-GCHC-OH is a Boc-protected, cis-configured amino acid derivative used as a stereochemically defined building block in peptide and peptidomimetic synthesis. Its protected amino functionality and defined side-chain geometry make it a practical intermediate for constructing constrained sequences where cis stereochemistry is important for conformational control in downstream targets.
1. Peptidomimetic Building Blocks
(Boc)2-4-cis-GCHC-OH is used by medicinal chemistry and peptide research groups to assemble constrained peptidomimetics and structure-guided analogs in which the cis side-chain arrangement is carried through to the final scaffold. The Boc-protected functionality supports routine peptide-coupling workflows for generating amide-linked intermediates, enabling incorporation into custom synthesis campaigns where stereochemical fidelity and protection strategy are critical for reliable sequence assembly.
2. Protected Amino Acid Intermediates
(Boc)2-4-cis-GCHC-OH serves as a protected amino acid intermediate for stepwise synthesis of larger peptide segments and advanced coupling precursors. Process development teams and custom peptide manufacturers rely on such protected derivatives to manage chemoselectivity during chain extension, allowing controlled introduction of the cis-configured residue into solution-phase or segment condensation workflows while maintaining compatibility with standard protected-amino-acid handling practices.
3. Stereodefined SAR Synthesis
(Boc)2-4-cis-GCHC-OH is selected for structure-activity relationship (SAR) studies where stereodefined analog libraries require consistent incorporation of a cis-configured motif. Research laboratories use this derivative to prepare series of closely related peptide-like compounds that differ by sequence context or side-chain modifications, with the protected form supporting reproducible downstream assembly and purification of intermediates used for biological screening collaborations.
4. Custom Peptide Manufacturing Research
(Boc)2-4-cis-GCHC-OH is applied in custom peptide manufacturing development when a specific cis stereochemical element must be introduced as a defined residue during synthesis planning. Peptide CROs and advanced synthesis groups use this intermediate to reduce variability between batches of complex, stereochemically sensitive targets, supporting reliable generation of peptide intermediates and final products for chemical biology tool development and research-grade library production.
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