Boc-cyclohexylstatine is a Boc-protected, non-proteinogenic amino acid derivative featuring a cyclohexyl-substituted statine backbone that functions as a sterically constrained analog of the amino acid family. The molecule contains an amino functionality masked as a tert-butoxycarbonyl (Boc) carbamate and a free carboxylic acid, with the cyclohexyl side chain providing a hydrophobic, conformationally restricted group for controlling side-chain presentation in synthetic sequences. As a protected amino acid building block, it is used in peptide chemistry to support stepwise assembly and chemoselective coupling while maintaining orthogonal reactivity of the carboxyl group for incorporation into more complex amino acid and peptide derivatives.
CAT No: CP27622
CAS No:98105-45-4
Synonyms/Alias:Boc-ACHPA;(3S,4S)-4-(Boc-amino)-5-cyclohexyl-3-hydroxy-pentanoic acid
Boc-cyclohexylstatine is a Boc-protected statine derivative featuring a cyclohexyl side chain, supplied as an amino acid building block for peptide and peptidomimetic assembly. The Boc group provides a protected amino functionality commonly leveraged in controlled coupling workflows, while the bulky, hydrophobic cyclohexyl substituent supports the development of sterically defined analogs used in protease-focused chemical biology and inhibitor design programs.
1. Peptidomimetic Synthesis
Boc-cyclohexylstatine is used by medicinal chemistry teams to construct statine-based peptidomimetics and constrained analogs that emulate key transition-state features in protease inhibitor research. Its Boc-protected amino group supports stepwise incorporation into peptide-like scaffolds, enabling the preparation of inhibitor series where side-chain sterics and hydrophobic character are tuned to probe structure-activity relationships. Researchers commonly employ this building block in solution-phase or automated peptide assembly workflows to generate analogs for downstream biochemical characterization and SAR mapping.
2. Protease Inhibitor Building Block
Boc-cyclohexylstatine is frequently selected as a specialty amino acid intermediate for assembling protease inhibitor candidates, particularly where statine motifs are used to create strong, enzyme-active-site-relevant binding interactions in peptidomimetic formats. The cyclohexyl side chain provides a hydrophobic, conformationally rich substituent that can enhance shape complementarity and drive systematic variation across inhibitor libraries. Chemical biology groups and process development chemists use this reagent to prepare structurally consistent intermediate fragments that can be carried into final inhibitor synthesis and analog generation.
3. Pharmaceutical Intermediate Development
Boc-cyclohexylstatine serves as a practical intermediate for manufacturing-scale preparation of statine-containing fragments used in custom synthesis and pharmaceutical intermediate programs. The protected amino functionality allows controlled downstream transformations during route development, supporting the preparation of defined stereochemical and functional-group patterns needed for late-stage assembly. Industrial and contract synthesis teams rely on this type of Boc-protected amino acid building block to streamline procurement of key scaffold elements for iterative medicinal chemistry and analog production campaigns.
4. SAR Library Construction
Boc-cyclohexylstatine is applied in parallel synthesis and library construction efforts where statine-derived residues are varied to map how hydrophobic bulk influences binding and selectivity trends. Researchers use the reagent to build a consistent backbone motif while swapping related side-chain analogs, enabling efficient generation of compound sets for comparative evaluation. This approach is especially common in discovery chemistry workflows that require reliable incorporation of a protected amino acid building block into multiple analogs with minimal variability across the statine region.
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