Boc-N-α-methyl-L-Phenylalanine is a protected amino acid derivative in which the amino terminus of L-phenylalanine is carbamated with a Boc (tert-butoxycarbonyl) group and the α-carbon bears an additional methyl substituent, classifying it as an N-Boc, α-methylated phenylalanine analogue. The molecule contains a free carboxylic acid and a Boc-protected amine, while the side chain remains a benzyl aromatic group that can participate in hydrophobic and π-interactions during peptide assembly. As a stepwise peptide synthesis building block, the Boc group provides chemoselective control over amide bond formation at the N-terminus, and the α-methyl substitution is commonly used in structure-activity and conformational studies to modulate backbone geometry and peptide properties.
CAT No: CP01641
CAS No:37553-65-4
Synonyms/Alias:Boc-N-Me-Phe-OH;37553-65-4;Boc-N-methyl-L-phenylalanine;Boc-Mephe-Oh;Boc-L-MePhe-OH;SBB064203;AmbotzBAA1113;PubChem12252;AC1Q3VRD;SCHEMBL65502;15551_ALDRICH;Boc-N-a-methyl-L-Phenylalanine;15551_FLUKA;CTK2A6497;AJGJINVEYVTDNH-LBPRGKRZSA-N;MolPort-001-793-456;ZINC2391122;ANW-42415;CB-642;t-butoxycarbonyl-N-methylphenylalanine;AKOS015836711;AKOS015889958;AJ-35718;AK-46141;AM808155
Boc-N-α-methyl-L-Phenylalanine is a Boc-protected, α-methylated phenylalanine derivative used as a stereochemically defined amino acid building block for peptide synthesis. The α-methyl substitution introduces steric and conformational effects relative to standard phenylalanine, while the Boc group provides an acid-labile N-protection strategy commonly leveraged in protected-amino-acid coupling workflows. This reagent is typically selected when researchers aim to incorporate an α-methyl residue into peptides or peptide-like structures to modulate backbone properties and improve synthetic control during assembly.
1. Peptide Backbone Modification
Boc-N-α-methyl-L-Phenylalanine is used by peptide chemists to introduce an α-methylated phenylalanine unit into custom peptide sequences where backbone sterics and local conformational bias are important design elements. The Boc-protected amine supports routine protected-amino-acid handling in peptide assembly workflows, enabling incorporation of a residue that differs from canonical phenylalanine at the backbone alpha position. This makes the building block particularly relevant for preparing peptide analogs used in structure-function studies, synthetic library construction, and medicinal chemistry lead optimization where subtle changes to residue geometry can influence downstream behavior of the peptide scaffold.
2. Protected Amino Acid Building Block
Boc-N-α-methyl-L-Phenylalanine serves as a defined, protected amino acid intermediate for stepwise synthesis of longer peptide segments and for the preparation of modified amino acid-containing fragments. Researchers developing non-standard peptide motifs rely on α-methylated residues to tune steric bulk around the backbone and to create distinct chemical environments for subsequent coupling steps and purification. In practical peptide manufacturing and research settings, the Boc protection pattern provides a widely used compatibility framework for assembling protected amino acid sequences, allowing this building block to be integrated into workflows that require precise residue identity and stereochemical consistency.
3. Peptidomimetic And SAR Studies
Boc-N-α-methyl-L-Phenylalanine is commonly selected in medicinal chemistry programs that generate peptidomimetic analogs for structure-activity relationship (SAR) investigations. Incorporating an α-methylated phenylalanine residue helps chemists explore how backbone substitution patterns affect the properties of peptide-like compounds, including how the scaffold presents functional groups and how it behaves during chemical derivatization and analytical characterization. The Boc-protected, fully defined amino acid form supports reproducible synthesis of analog series, which is valuable for comparing structure-defined variants in screening campaigns and follow-up characterization work.
4. Pharmaceutical Intermediate Development
Boc-N-α-methyl-L-Phenylalanine is also used as a pharmaceutical intermediate building block in the preparation of larger, peptide-derived chemical entities during process development and custom synthesis. Teams developing modified amino acid motifs for candidate molecules often require reliable access to protected, stereochemically defined α-substituted residues that can be carried through multi-step assembly into final intermediates. The presence of the Boc-protected N-terminus and the α-methyl substitution makes this reagent a practical choice for constructing intermediate structures that incorporate backbone-modified phenylalanine units, supporting downstream conversion into advanced synthetic targets used in research and industrial chemical development.
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