Boc-D-Phenylalanine is a protected, non-natural stereochemical form of phenylalanine in which the amino group is protected with a Boc (tert-butoxycarbonyl) group and the side chain retains the benzyl aromatic functionality characteristic of phenylalanine. The molecule bears a free carboxylic acid and a Boc-protected amine, with the D stereochemical configuration indicated by the product name, enabling chemoselective handling of the amino functionality during stepwise coupling. It is employed as an amino acid building block for peptide synthesis and for preparing peptide-related intermediates where controlled amide-bond formation at the carboxylate/amine pair is required while the Boc group suppresses undesired side reactions of the amine.
CAT No: CP01608
CAS No:18942-49-9
Synonyms/Alias:Boc-D-phenylalanine;N-Boc-D-phenylalanine;18942-49-9;Boc-D-Phe-OH;N-(tert-Butoxycarbonyl)-D-phenylalanine;ZYJPUMXJBDHSIF-LLVKDONJSA-N;SBB063179;(TERT-BUTOXYCARBONYL)-D-PHENYLALANINE;d-Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-;(2R)-2-[(tert-butoxy)carbonylamino]-3-phenylpropanoicacid;(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoicacid;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-PHENYLPROPANOICACID;Boc-D-phenyl-alanine;AC1LCULB;PubChem10968;BOC-D-PHE;AC1Q1MTQ;N-[-(1,1-Dimethylethoxy)-carbonyl]-D-phenylamine;KSC174S5P;15484_ALDRICH;SCHEMBL606309;Jsp003893;N-T-BOC-D-PHENYLALANINE;t-butoxycarbonyl-D-phenylalanine;15484_FLUKA
Boc-D-Phenylalanine is a D-configured phenylalanine building block bearing an N-terminal Boc protecting group, making it a protected amino acid commonly used to control amide formation and prevent unwanted side reactions during peptide assembly. Its benzyl side chain provides the hydrophobic aromatic functionality typical of phenylalanine, while the Boc group supports established protected-amino-acid workflows in peptide chemistry and intermediate preparation.
1. Boc-Based Peptide Synthesis
Boc-D-Phenylalanine is used as an amino acid building block for constructing peptides and peptide segments that require incorporation of D-phenylalanine at defined positions. Custom peptide synthesis teams and peptide reagent users rely on its protected N-terminus to maintain chemoselectivity during coupling steps, enabling consistent formation of amide bonds while minimizing side reactions from the amino functionality. The D-configuration supports stereochemical control in peptide design, including the preparation of stereochemically defined analogs used in structure-property studies and peptide library work.
2. D-Amino Acid Segment Building
Boc-D-Phenylalanine serves as a practical starting unit for assembling D-amino-acid-containing segments used in modified peptide development and SAR-style optimization. Researchers preparing stereochemically defined intermediates often choose a Boc-protected form to match their downstream deprotection and coupling sequence, particularly when building longer sequences from protected amino acid components. The aromatic side chain characteristic of phenylalanine also supports incorporation into hydrophobic peptide regions, which is frequently important for maintaining defined conformational tendencies in synthetic peptide frameworks.
3. Pharmaceutical Intermediate Development
Boc-D-Phenylalanine is also used as a protected amino acid intermediate in medicinal chemistry and pharmaceutical intermediate programs where D-phenylalanine-containing motifs are required. Process chemists and intermediate developers value protected amino acid reagents for their predictable handling and compatibility with stepwise synthesis strategies that build toward amide-containing structures. In this context, Boc-D-Phenylalanine provides a stereochemically defined, functionally protected precursor that can be carried through to downstream coupling or derivatization steps used to generate advanced intermediates for further development.
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