Boc-4-tert-butyl-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino group is masked as a Boc carbamate and the side chain is a phenylalanine framework bearing a 4-tert-butyl substituent on the aromatic ring. The molecule contains a free carboxylic acid functional group and a stereochemically specified D-configuration at the alpha carbon, with the tert-butyl group increasing the hydrophobic character of the aromatic side chain while the Boc group controls chemoselectivity by preventing unprotected amine reactivity during coupling steps. In peptide chemistry and structure-activity studies, this protected analogue is used as a building block for introducing a bulky, hydrophobic aromatic residue into peptides or peptide-related intermediates, supporting stepwise synthesis and subsequent deprotection to generate the corresponding free amino functionality.
CAT No: CP11305
CAS No:250611-12-2
Synonyms/Alias:250611-12-2;Boc-4-tert-butyl-D-Phe-OH;Boc-4-tert-butyl-D-phenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(4-(tert-butyl)phenyl)propanoicacid;BOC-D-4-TERT-BUTYL-PHE;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-tert-butylphenyl)propanoicacid;BOC-P-TBU-D-PHE-OH;BOC-D-4-TBU-PHE-OH;BOC-D-PHE(4-TBU)-OH;SCHEMBL14250514;05839_FLUKA;BOC-P-TBU-D-PHE-OHDCHA;MolPort-001-758-552;BOC-D-PHE(4-TBU)-OHDCHA;ZINC2389806;1954AB;BOC-4-T-BUTYL-D-PHENYLALANINE;AB10914;AM82727;BOC-D-4-TERT-BUTYLPHENYLALANINE;BOC-D-4-TETR-BUTYLPHENYLALANINE;CB-1277;OR14622;AJ-35626;AK114801
Boc-4-tert-butyl-D-Phenylalanine is a protected, D-configured phenylalanine derivative bearing a Boc-protected alpha-amino group and a 4-tert-butyl substituted aromatic side chain. This sterically bulky, hydrophobic side chain is frequently used to introduce conformational and physicochemical character into peptide sequences while maintaining orthogonality and stability during peptide assembly. As a Boc amino acid building block, it is commonly selected for stepwise peptide synthesis workflows that require reliable N-terminal protection and a non-natural side-chain substitution pattern.
1. Boc-Based Peptide Synthesis
Boc-4-tert-butyl-D-Phenylalanine is used as an amino acid building block for solution-phase and solid-phase peptide synthesis where Boc protection aligns with standard deprotection and coupling strategies. Researchers incorporate this D-amino acid into peptide segments to probe how stereochemistry and a bulky 4-tert-butyl aromatic side chain influence folding propensity, local hydrophobicity, and resistance to proteolytic processing in peptide analogs. Peptide chemists also favor this protected form for assembling defined sequences in custom peptide synthesis, including libraries of stereochemically constrained or hydrophobicity-tuned analogs.
2. Peptidomimetic And SAR Studies
Boc-4-tert-butyl-D-Phenylalanine supports medicinal chemistry workflows that build peptidomimetics and non-natural peptide analogs for structure-activity relationship (SAR) exploration. The D-configuration and 4-tert-butyl substituted phenyl side chain provide a practical handle to modulate steric bulk and aromatic character without changing the peptide backbone connectivity. In practice, medicinal chemistry groups use this building block to generate analog series where sequence stereochemistry and side-chain hydrophobicity are systematically varied, enabling downstream evaluation of physicochemical properties and target engagement readouts in chemical biology assays.
3. Conformational Control In Analog Design
Boc-4-tert-butyl-D-Phenylalanine is commonly chosen when peptide design requires stronger conformational and microenvironment control from side-chain substitution. The 4-tert-butyl group increases steric demand around the aromatic ring, which can affect intramolecular packing and the local presentation of functional groups along the peptide. Protein and peptide engineering researchers use such analogs to create sequence variants that mimic or disrupt specific structural motifs, supporting studies of structure-function relationships in synthetic peptide materials, binding assays, and mechanistic chemical biology experiments.
4. Pharmaceutical Intermediate Building Block
Boc-4-tert-butyl-D-Phenylalanine is also utilized as a protected amino acid intermediate for downstream preparation of specialized peptide fragments and non-natural amino acid derivatives used in pharmaceutical intermediate development. Process chemistry and custom synthesis teams rely on the Boc-protected, stereodefined starting material to construct defined building blocks for further derivatization and segment coupling. This makes it a practical reagent for manufacturing workflows that require consistent stereochemical identity and a stable protected form during multi-step assembly of complex peptide-based intermediates.
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