Boc-4-Methy-D-Phenylalanine contains an amino acid backbone bearing a benzyl-type aromatic side chain substituted with a 4-methyl group, and it is presented as the D stereoisomer. The amino group is protected as a Boc carbamate, while the carboxyl functionality remains available for conversion into peptide-coupling derivatives, enabling controlled chemoselectivity during stepwise assembly of peptide chains. In peptide chemistry and chemical biology workflows, this protected, stereodefined amino acid derivative is used as a building block to introduce the 4-methyl-substituted phenylalanine motif into synthetic peptides and related amino acid conjugates.
CAT No: CP15805
CAS No:80102-27-8
Synonyms/Alias:80102-27-8;Boc-4-methyl-D-phenylalanine;Boc-D-Phe(4-Me)-OH;(R)-2-((tert-Butoxycarbonyl)amino)-3-(p-tolyl)propanoic acid;BOC-D-4-METHYLPHE;(2R)-3-(4-methylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;MFCD01317726;BOC-P-ME-D-PHE-OH;N-((1,1-Dimethylethoxy)carbonyl)-4-methyl-D-phenylalanine;N-[(1,1-Dimethylethoxy)carbonyl]-4-methyl-D-phenylalanine;D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-methyl-;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-methylphenyl)propanoic acid;SCHEMBL5061931;DTXSID70426511;JYRWNPUFECDJCX-GFCCVEGCSA-N;AKOS016843545;AC-9929;PS-12013;CS-0153094;A50135;EN300-3389905;N-(tert-butoxycarbonyl)-4-methyl-D-phenylalanine;Boc-D-4-Methylphenylalanine (Boc-D-Phe(4-Me)-OH);(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-P-TOLYLPROPANOIC ACID;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-methylphenyl)propanoic acid;
Boc-4-Methy-D-Phenylalanine is a Boc-protected D-configured phenylalanine derivative bearing a 4-methyl substituent on the aromatic ring. As a protected amino acid building block, it is designed for controlled incorporation into peptide sequences using Boc-based synthetic workflows, where the stereochemistry and side-chain electronics/sterics can be leveraged for structure-activity relationship studies and selective analog generation. The Boc group provides a stable handle for stepwise assembly, while the substituted phenyl side chain supports downstream medicinal chemistry optimization of peptide-like scaffolds and peptidomimetics.
1. Boc-Based Peptide Synthesis
Boc-4-Methy-D-Phenylalanine is used by peptide synthesis groups to introduce a D-amino acid residue with a para-methyl substituted phenyl side chain into defined peptide analogs. Researchers in custom peptide manufacturing and medicinal chemistry commonly select this building block when they want stereochemical control (D-configuration) and a modulated aromatic environment to tune properties such as conformation and structure-activity relationships in peptide series. The Boc protection pattern supports routine stepwise coupling strategies in Boc chemistry workflows, enabling reliable construction of short to medium-length peptide segments and analog libraries.
2. Peptidomimetic SAR Building Block
Boc-4-Methy-D-Phenylalanine is frequently employed in peptidomimetic development where aromatic side-chain substitution and D-stereochemistry are used to generate systematic structure-activity relationship (SAR) variants. Medicinal chemistry teams use this derivative to prepare analog panels that probe how changes to the para-substituted phenyl ring influence physicochemical behavior and target interaction profiles within peptide-like leads. Because the residue is pre-functionalized as a protected amino acid, it fits cleanly into downstream fragment assembly and analog diversification workflows used for lead optimization and structure-guided design.
3. Stereochemically Defined Analog Production
Boc-4-Methy-D-Phenylalanine supports the production of stereochemically defined peptide and peptide-mimic standards used in chemical biology and analytical method development. Laboratories that build reference compounds for LC-MS characterization, purity verification, and comparative profiling of peptide analogs rely on D-amino acid-containing sequences to distinguish stereochemical variants and reduce ambiguity when multiple closely related analogs are synthesized. The Boc-protected format streamlines incorporation into the target sequence during synthesis planning, helping teams generate consistent analogs for method validation and compound library quality control.
4. Pharmaceutical Intermediate Diversification
Boc-4-Methy-D-Phenylalanine is also used as a pharmaceutical intermediate building block in the synthesis of substituted D-amino acid motifs that feed into larger medicinal chemistry programs. Process and development chemists incorporate this residue into intermediate scaffolds to access protected D-aromatic amino acid fragments that can be further elaborated into peptide-derived candidates, constrained analogs, or specialized linker-containing intermediates. The combination of Boc protection and the para-methyl phenyl side chain makes it a practical starting point for creating defined stereochemical and substitution patterns early in a synthetic route, which is valuable for downstream scale-up planning and analog series consistency.
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