Boc-2-Methoxy-L-Phenylalanine is a Boc-protected, naturally occurring amino acid derivative in which the phenylalanine side chain is substituted at the alpha position with a methoxy group, yielding a nonstandard amino acid building block for peptide-related synthesis. The molecule contains a Boc-protected amino functional group and a free carboxylic acid, while the side chain bears a benzyl aromatic ring and the 2-methoxy substitution provides an ether functionality that can influence polarity and steric profile during coupling and subsequent transformations. In synthetic peptide workflows, the Boc group controls chemoselectivity by masking the amine during stepwise assembly, and the 2-methoxy modification can be used in structure-activity and chemical biology studies to probe how alpha-ether substitution affects peptide conformation, physicochemical properties, and labeling strategies.
CAT No: CP15304
Synonyms/Alias:Boc-2-Methoxy-L-Phenylalanine;143415-63-8;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-methoxyphenyl)propanoic acid;(2S)-3-(2-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;MFCD01860640;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2-methoxyphenyl)propanoic acid;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(2-METHOXYPHENYL)PROPANOIC ACID;SCHEMBL3376442;QMHKMTAKTUUKEK-NSHDSACASA-N;Boc-2-methoxy-L-phenylalanine, 97%;HY-W141812;AS-82413;DA-51272;CS-0201609;N10883;(S)-2-tert-Butoxycarbonylamino-3-(2-methoxyphenyl)propionic acid;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID;
Boc-2-Methoxy-L-Phenylalanine is a Boc-protected amino acid derivative featuring an L-phenylalanine backbone with a 2-methoxy substituent on the aromatic ring. This protected form is commonly used as a building block for peptide and peptidomimetic synthesis where the Boc group enables controlled N-terminus assembly, while the ortho-methoxy functionality provides an electronically and sterically distinct side chain for structure-activity and conformational studies. Researchers select this derivative when they need an aromatic methoxy-bearing phenylalanine unit that can be incorporated into defined sequences or used as a pharmaceutical intermediate precursor.
1. Peptide Building Block
Boc-2-Methoxy-L-Phenylalanine supports custom peptide synthesis workflows where a protected aromatic phenylalanine variant is required for sequence-defined assembly. Peptide chemists use this building block to introduce an ortho-methoxy substituted aromatic side chain that can influence local polarity, steric environment, and aromatic electronics in the resulting peptide. The Boc-protected amino functionality is particularly convenient for stepwise coupling strategies in which the N-terminus must be protected during chain elongation, enabling reliable incorporation into short to medium-length peptides and peptide analogs for SAR (structure-activity relationship) studies.
2. Peptidomimetic Medicinal Chemistry
Boc-2-Methoxy-L-Phenylalanine is frequently used in medicinal chemistry programs that generate peptidomimetics and constrained analogs to probe how aromatic substitution patterns affect binding interactions and overall molecular recognition. Medicinal chemistry teams value the 2-methoxy substitution for introducing a defined hydrogen-bond acceptor site and modifying aromatic character without changing the core phenylalanine scaffold. As a Boc-protected intermediate, it fits into downstream synthesis routes that assemble larger fragments or final analogs, helping researchers systematically vary aromatic substitution to map structure-property trends.
3. Pharmaceutical Intermediate Synthesis
Boc-2-Methoxy-L-Phenylalanine is also used as a protected amino acid intermediate for the preparation of substituted aromatic amino acid derivatives and related synthetic intermediates. Process and development chemists rely on Boc protection to manage reactivity during multi-step sequences, especially when the target route requires controlled handling of the amino functionality while further functionalization or fragment coupling is performed. This makes the compound a practical input for manufacturing-oriented synthesis planning where orthogonal reactivity control and reliable downstream conversion to other derivatives are required.
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