Boc-L-cyclohexylalanine is an N-Boc-protected amino acid derivative of L-cyclohexylalanine, featuring a cyclohexyl side chain that classifies it as a nonpolar, hydrophobic amino acid analogue. The molecule contains a free carboxylic acid and an amine masked as a tert-butoxycarbonyl (Boc) carbamate, with stereochemistry specified as L at the alpha carbon. In peptide chemistry, this protected analogue is used as a stepwise coupling building block in peptide synthesis workflows where the Boc group controls chemoselectivity by suppressing unprotected amine reactivity while the carboxyl group provides the acyl functionality for forming peptide bonds.
CAT No: CP21007
CAS No:37736-82-6
Synonyms/Alias:37736-82-6;Boc-Cha-OHhydrate;BOC-BETA-CYCLOHEXYL-ALA-OH;(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclohexylpropanoicacid;Boc-Cha-OH;Boc-L-cyclohexylalanine;(S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionicacid;Boc-hexahydro-L-phenylalanine;N-BOC-b-cyclohexylalanine;Boc-3-cyclohexyl-L-alanine;N-BOC-beta-cyclohexylalanine;SCHEMBL16946;15477_ALDRICH;15477_FLUKA;CTK7I3134;MolPort-000-006-466;MSZQAQJBXGTSHP-NSHDSACASA-N;ACT10811;ZINC2554975;ANW-43621;MFCD00211335;RW1238;SBB065824;AKOS015892630;t-butoxycarbonyl-3-cyclohexyl-L-alanine
Boc-L-cyclohexylalanine is an L-amino acid building block bearing a Boc-protecting group on the alpha-amino functionality and a cyclohexyl side chain that provides a bulky, hydrophobic character. This protected amino acid is commonly used in peptide synthesis workflows where controlled amine protection and side-chain hydrophobicity are important for assembling peptides and peptide-like intermediates with defined stereochemistry. Its Boc protection makes it a practical component for stepwise coupling strategies in the preparation of protected peptide segments and medicinal chemistry precursors.
1. Solid-Phase Peptide Building
Boc-L-cyclohexylalanine is used by peptide synthesis groups to introduce a hydrophobic cyclohexyl side chain into peptide sequences while maintaining a protected alpha-amino group during chain assembly. Researchers preparing protected peptide fragments and final peptide targets rely on the Boc functionality to support controlled coupling and subsequent deprotection steps within their established peptide manufacturing workflows. The bulky, nonpolar side chain helps tune local sterics and hydrophobic surface properties, which is often relevant for structure-activity relationship (SAR) studies and for generating peptide scaffolds with improved conformational preferences for downstream evaluation.
2. Solution-Phase Segment Coupling
Boc-L-cyclohexylalanine is frequently selected for solution-phase peptide synthesis where protected amino acid residues are condensed into defined segments prior to final assembly. Medicinal chemistry teams and custom peptide manufacturing laboratories use this Boc-protected building block to incorporate L-cyclohexylalanine residues with consistent stereochemical definition and hydrophobic side-chain character. In these workflows, the Boc-protected amine supports compatibility with common peptide segment strategies, enabling the preparation of longer, more complex intermediates used for subsequent purification and characterization by HPLC and mass spectrometry.
3. Peptide Medicinal Chemistry Intermediates
Boc-L-cyclohexylalanine is applied in the development of peptide-based leads and peptidomimetic-like analogs where residue-level hydrophobicity and steric bulk are used to modulate peptide properties during lead optimization. Chemical biology and medicinal chemistry groups incorporate this protected amino acid into candidate sequences to generate analog libraries for SAR mapping, with the cyclohexyl side chain serving as a strong hydrophobic substituent that can influence helix/turn propensity and overall peptide shape. The Boc-protected format supports its role as a reliable intermediate for assembling candidate structures that are later advanced into biological testing workflows by downstream partners.
4. Protected Amino Acid Library Synthesis
Boc-L-cyclohexylalanine is also used in parallel synthesis and library-building efforts where standardized protected amino acid building blocks are required for reproducible residue incorporation. Research teams constructing small-molecule-like peptide libraries for screening or mechanistic studies often prefer Boc-protected amino acids because they fit established deprotection and coupling schedules used to generate series of analogs differing by one or more residues. The cyclohexylalanine side chain provides a distinct hydrophobic motif that helps diversify chemical space while keeping the backbone chemistry consistent across the library, supporting efficient comparative analysis of structure-property relationships.
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