Boc-D-cyclohexylalanine is a Boc-protected D-form amino acid derivative in which the side chain is a cyclohexyl group attached to the α-carbon, classifying it as a non-natural, hydrophobic amino acid analogue for peptide chemistry. The molecule contains a carbamate-protected amino group (Boc) and a free carboxylic acid functional group, with the D stereochemical configuration indicated by the product name and the cyclohexyl side chain providing conformationally constrained, nonpolar character. In synthesis, this protected amino acid is used as a building block for stepwise peptide assembly where the Boc group controls chemoselectivity by masking the amine during coupling, supporting the incorporation of a bulky, hydrophobic residue into peptide and peptide-mimetic structures.
CAT No: CP21006
CAS No:127095-92-5
Synonyms/Alias:127095-92-5;Boc-D-Cha-OH;(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclohexylpropanoicacid;Boc-D-Cha-OHhydrate;Boc-D-cyclohexylalanine;Boc-3-cyclohexyl-D-alanine;Boc-hexahydro-D-phenylalanine;Boc-3-cyclohexyl-D-alaninehydrate;Boc-beta-cyclohexyl-D-alaninemonohydrate;(2R)-2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoicacid;(2R)-2-[(tert-butoxycarbonyl)amino]-3-cyclohexylpropanoicacid;AmbotzBAA1314;AC1MBSEJ;AC1Q1MTZ;15476_ALDRICH;SCHEMBL482062;N-Boc-beta-cyclohexyl-D-alanine;15476_FLUKA;CTK8C5093;CYCLOHEXANEPROPANOICACID,A-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-,(AR)-;MolPort-003-725-628;MSZQAQJBXGTSHP-LLVKDONJSA-N;ACT09062;ZINC2504643;ANW-74101
Boc-D-cyclohexylalanine is a D-configured cyclohexyl-substituted amino acid supplied as the Boc-protected building block, making it a common chiral intermediate for peptide and peptidomimetic synthesis. Its bulky, hydrophobic side chain supports incorporation into sequences where steric bulk and nonpolar character are used to modulate conformation and local interactions. As a protected amino acid, it is typically handled as a synthetic precursor for downstream coupling rather than as a free amino acid reagent.
1. Peptide Building Block Use
Boc-D-cyclohexylalanine is used by peptide synthesis groups to introduce a D-amino acid residue bearing a cyclohexyl side chain into custom peptides and peptidomimetic scaffolds. Solid-phase and solution-phase peptide workflows rely on Boc-protected amino acids as coupling-ready intermediates, enabling controlled assembly of stereodefined sequences. The cyclohexyl group provides a strongly hydrophobic, sterically demanding side chain that is frequently selected when researchers aim to probe structure-property relationships, including effects of backbone stereochemistry and side-chain bulk on peptide conformation.
2. Peptidomimetic SAR Studies
Boc-D-cyclohexylalanine is frequently incorporated into medicinal chemistry programs focused on peptidomimetic development and structure-activity relationship (SAR) studies. Synthetic teams use D-configured, nonpolar residues to tune physicochemical properties such as hydrophobic surface character and to explore how stereochemical inversion at the residue level influences the overall peptide-like framework. The Boc-protected form supports routine preparation of analog libraries where the cyclohexylalanine unit serves as a hydrophobic "handle" for systematic variation of side-chain size and steric profile.
3. Chiral Intermediate For Derivatization
Boc-D-cyclohexylalanine is also used as a chiral amino acid intermediate for downstream derivatization into specialized building blocks for complex organic synthesis. Process and development chemists value the combination of stereochemical control (D-configuration) and the Boc-protected amine for constructing further functionalized derivatives while maintaining defined stereochemistry at the α-carbon. In practice, this supports the preparation of advanced intermediates used in the synthesis of modified peptide segments, constrained analogs, and other stereodefined structures where the cyclohexyl side chain is retained as a key structural element.
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