N-Boc-3-hydroxy-D-phenylalanine features an aromatic ring with a hydroxyl substitution and a protected amino group. Researchers use it to probe stereochemical effects, hydrogen-bond modulation, and aromatic stacking. The D-configuration offers contrast in folding pathways and enzymatic processing. Boc protection ensures controlled solid-phase incorporation.
CAT No: R2155
CAS No:90819-32-2
Synonyms/Alias:N-BOC-3-HYDROXY-D-PHENYLALANINE;90819-32-2;Boc-D-phe(3-OH)-OH;(R)-2-((tert-Butoxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoic acid;MFCD07371959;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-hydroxyphenyl)propanoic acid;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-hydroxyphenyl)propanoic acid;SCHEMBL9956884;CS-0434960;A50509;EN300-3372294;(2R)-3-(3-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;
N-Boc-3-hydroxy-D-phenylalanine is a synthetic amino acid derivative characterized by the presence of a tert-butyloxycarbonyl (Boc) protecting group on the amino functionality and a hydroxyl substitution at the 3-position of the phenyl ring. As a non-canonical amino acid, it offers unique structural and physicochemical properties that extend its value in biochemical research and peptide synthesis. The stereochemistry of the D-enantiomer further distinguishes it, enabling the exploration of chirality-dependent phenomena in biological and chemical systems. Its incorporation into peptides or small molecules can modulate molecular recognition, stability, and bioactivity, making it an important tool for researchers investigating structure-function relationships and synthetic strategies in the life sciences.
Peptide Synthesis: In solid-phase and solution-phase peptide synthesis, N-Boc-3-hydroxy-D-phenylalanine serves as a versatile building block for the introduction of non-proteinogenic residues. The Boc protection on the alpha-amino group allows for selective deprotection under mild acidic conditions, facilitating sequential coupling reactions. The 3-hydroxy functional group on the aromatic ring provides an additional handle for further chemical modification or for probing hydrogen bonding networks within peptides. Its D-configuration introduces conformational constraints that can enhance resistance to proteolytic degradation, enabling the design of more stable peptide analogs for biochemical studies.
Structure-Activity Relationship (SAR) Studies: The unique substitution pattern and chirality of this amino acid analog make it an invaluable probe in SAR investigations. By incorporating it into peptide sequences or small-molecule frameworks, researchers can systematically evaluate the effects of aromatic hydroxylation and D-stereochemistry on binding affinity, selectivity, and molecular recognition. These insights are crucial for the rational design of ligands, inhibitors, or molecular probes targeting enzymes, receptors, and other biomolecular assemblies.
Enzyme Specificity and Mechanistic Studies: N-Boc-3-hydroxy-D-phenylalanine is frequently utilized in enzymology to explore substrate specificity and catalytic mechanisms of proteases and amino acid-modifying enzymes. Its structural deviation from natural L-phenylalanine allows researchers to assess the stereochemical requirements of enzyme active sites and to identify key interactions that govern substrate turnover. The presence of the 3-hydroxy group can also mimic post-translational modifications or metabolic intermediates, providing a platform for mechanistic dissection.
Development of Modified Peptide Libraries: The compound is valuable for constructing combinatorial peptide libraries with enhanced chemical diversity. Incorporation of D- and non-standard amino acids such as 3-hydroxy-D-phenylalanine expands the accessible chemical space, facilitating the identification of novel bioactive sequences with improved pharmacokinetic and stability profiles. Such libraries are instrumental in high-throughput screening campaigns aimed at discovering new ligands, enzyme substrates, or molecular scaffolds for research applications.
Analytical and Diagnostic Research: As a structurally defined amino acid analog, N-Boc-3-hydroxy-D-phenylalanine is employed as a reference standard or internal control in chromatographic and spectrometric analyses. Its distinct physicochemical properties, including altered retention times and mass spectral signatures, support the development and validation of analytical methods for peptide mapping, purity assessment, and metabolic profiling. These applications are essential for ensuring the reliability and reproducibility of experimental data in biochemical research and quality control workflows.
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