Fmoc-D-Phenylalanine is a protected amino acid derivative in which the amino group of D-phenylalanine is capped with the 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) protecting group and the carboxylic acid remains available for coupling. The molecule contains the stereochemically defined D-configuration at the α-carbon, a benzyl side chain typical of phenylalanine, and both an Fmoc-protected amine and a free carboxyl functional group for controlled reactivity. Employed as a building block for stepwise peptide synthesis, it supports chemoselective amide bond formation at the carboxyl group while the Fmoc group serves to regulate the amine during sequential assembly and purification of peptide intermediates.
CAT No: CP01616
CAS No:86123-10-6
Synonyms/Alias:Fmoc-D-phenylalanine;Fmoc-D-Phe-OH;86123-10-6;N-Fmoc-D-phenylalanine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoicacid;CHEMBL348015;MFCD00062955;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-phenylalanine;N-(9-FLUORENYLMETHOXYCARBONYL)-D-PHENYLALANINE;fmoc-d-phe;AC1LJQNI;PubChem10030;KSC496O5B;47378_ALDRICH;SCHEMBL118169;AC1Q719T;47378_FLUKA;CTK3J6750;MolPort-003-934-090;SJVFAHZPLIXNDH-JOCHJYFZSA-N;ZINC4389106;N-ALPHA-FMOC-D-PHENYLALANINE;ANW-38280;BDBM50121969;CF-194
Fmoc-D-Phenylalanine is a D-configured phenylalanine derivative bearing a fluorenylmethyloxycarbonyl (Fmoc) group on the amino functionality and a free carboxylic acid suitable for peptide coupling. The stereogenic center at the α-carbon fixes the D-configuration, enabling incorporation of enantiomerically defined peptide segments for stereochemical studies and unnatural amino acid strategies. The phenyl side chain provides an aromatic handle for hydrophobic packing, π-π interactions, and downstream functionalization via electrophilic aromatic substitution or oxidative transformations. The Fmoc carbamate and carboxylic acid combine protection-controlled reactivity: the Fmoc group can be removed under base conditions to reveal an amine for iterative synthesis, while the acid participates in amide bond formation using standard peptide coupling chemistries.
1. Peptide Synthesis
Fmoc-D-Phenylalanine is used in peptide building-block preparation where the Fmoc-protected D-amino acid supports stepwise solid-phase or solution-phase coupling. The carboxylic acid and Fmoc-protected amine arrangement enables controlled amide bond formation to generate D-Phe-containing sequences with defined stereochemistry at the residue. The aromatic phenyl side chain supports formation of hydrophobic cores in peptides and can influence solubility and conformational preferences during synthesis and purification. Downstream, D-phenylalanine incorporation can be applied to generate peptide analogs for material scaffolds, stability studies, and stereochemically resolved sequence libraries that remain compatible with iterative Fmoc deprotection cycles.
2. Peptidomimetics And SAR Studies
Fmoc-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship investigations where D-amino acid substitution is used to tune backbone conformation and proteolytic resistance. The D-configuration at the α-carbon changes stereochemical presentation of the phenyl side chain relative to L-analogues, which can alter binding-site complementarity in receptor or enzyme assays. The Fmoc-protected amine supports rapid assembly of analog series, while the free carboxylic acid enables uniform coupling handles for generating consistent analog scaffolds. The resulting D-Phe-containing peptide fragments can serve as modular units for SAR panels, fragment coupling, and downstream derivatization into constrained or cyclized peptidomimetics.
3. Chemical Biology Labeling
Fmoc-D-Phenylalanine is suitable for chemical biology workflows that require stereodefined aromatic amino acid residues for tagging, probe construction, or affinity reagent synthesis. The phenyl side chain can be used as a site for chemical modification or as an aromatic reporter element in binding and crosslinking strategies, while the protected α-amine allows controlled incorporation into larger conjugates. Fmoc deprotection provides an orthogonal handle for subsequent conjugation steps, including attachment to linkers, solid supports, or biomolecule-reactive moieties. D-Phe-containing probes can be incorporated into peptide-based sensors or affinity ligands to probe stereochemical recognition and to generate stable labeling reagents for biochemical research intermediate preparation.
4. Protein Engineering
Fmoc-D-Phenylalanine can be employed in protein engineering and protein-surface modification contexts where D-amino acid residues are introduced to modulate local structure, stability, or interaction profiles. The Fmoc-protected backbone functionality supports synthesis of D-Phe-containing peptide segments that can be used as building blocks for ligation, conjugation, or incorporation into engineered constructs. The aromatic side chain contributes to hydrophobic interactions and can serve as a structural anchor within designed interfaces, while the D-configuration enables stereochemical control distinct from canonical L-amino acid patterns. The resulting D-Phe-bearing fragments may be used to generate engineered peptides for mapping interaction surfaces, designing protease-resistant domains, or preparing functional biomolecule conjugates.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-D-Phenylalanine is relevant to pharmaceutical manufacturing and fine chemical synthesis as a protected amino acid intermediate for producing D-amino acid-containing peptide intermediates. The Fmoc carbamate provides a robust protection strategy during storage and handling, while the free carboxylic acid enables conversion into activated coupling derivatives for downstream amide bond formation in controlled manufacturing routes. The stereodefined D-phenylalanine residue supports consistent incorporation into active pharmaceutical ingredient (API) intermediates, peptide-like intermediates, or process-grade peptidomimetic scaffolds. The compound's compatibility with standard peptide coupling and iterative deprotection logic makes it suitable for scalable intermediate preparation where stereochemical fidelity and reproducible coupling are required.
6. Analytical Research Standards
Fmoc-D-Phenylalanine is used in analytical research as a stereodefined reference material for method development, LC-MS/MS characterization, and peptide fragment identification involving D-phenylalanine residues. The Fmoc group and carboxylic acid functionality enable incorporation into synthetic peptides or standards that mimic target analytes, improving traceability of stereochemical assignments and fragmentation behavior. The aromatic side chain contributes characteristic ionization and fragmentation patterns that can support targeted analytical workflows for peptide stereochemistry verification. The resulting D-Phe-containing standards can be applied in impurity profiling, stability-indicating method development, and analytical reference preparation for amino acid derivative characterization.
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