L-DiPhenylalanine contains two phenyl-substituted side-chain moieties attached to an α-amino acid backbone, classifying it as a nonstandard, aromatic amino acid derivative relative to proteinogenic phenylalanine. The molecule bears a free α-amino group and a free carboxyl group along with an L-stereochemical designation, and its hydrophobic, π-rich side chain functionality can support aromatic stacking and increased conformational bias in peptide contexts. L-DiPhenylalanine is used in peptide synthesis and structure-activity or material-oriented studies where incorporation of a bulky, aromatic-rich residue is used to tune secondary structure, binding interfaces, and analytical behavior of peptide or amino-acid-derived constructs.
CAT No: CP17101
CAS No:149597-92-2
Synonyms/Alias:149597-92-2;(S)-2-amino-3,3-diphenylpropanoic acid;3,3-Diphenyl-L-alanine;L-3,3-Diphenylalanine;L-Diphenylalanine;(2S)-2-amino-3,3-diphenylpropanoic acid;L-Phenylalanine, beta-phenyl-;beta-Phenyl-L-phenylalanine;L1ZWG54X8B;MFCD01631989;3,3-Diphenylalanine;(S)-2-Amino-3,3-diphenyl-propionic acid;UNII-L1ZWG54X8B;(2S)-2-azaniumyl-3,3-diphenylpropanoate;.BETA.-PHENYL-L-PHENYLALANINE;L-PHENYLALANINE, .BETA.-PHENYL-;H-Dph-OH;beta-Phenylphenylalanine;(2S)-2-amino-3,3-diphenyl-propanoic acid;(S)-2-Amino-3,3-diphenylpropionic acid;(S)-2-Amino-3,3-diphenylpropanoicacid;--Phenyl-L-phenylalanine;SCHEMBL43672;DTXSID50978220;PECGVEGMRUZOML-AWEZNQCLSA-N;AKOS017344553;AC-4455;CS-W008077;HY-W008077;L-3,3-Diphenylalanine (H-L-Dip-OH);DS-10773;DB-005553;3,3-Diphenyl-L-alanine, >=98.0% (HPLC);EN300-6473088;
L-DiPhenylalanine is a chiral amino acid derivative related to the phenylalanine scaffold, featuring two stereogenic centers associated with the L-configuration at the amino acid framework and a side chain dominated by benzylic aryl functionality. The molecule contains an amino group and a carboxylic acid (or acid-equivalent functionality depending on the supplied form), enabling formation of amide and peptide bonds while also supporting salt formation and controlled solubility. The two phenyl rings provide strong hydrophobic and π-interaction surfaces that influence conformational preferences in peptide-like assemblies and can drive aggregation behavior in materials contexts. As a stereochemically defined, aromatic-rich building block, L-DiPhenylalanine functions as a practical intermediate for protected amino acid chemistry, peptide coupling chemistry, and downstream derivatization where aromatic side-chain reactivity and chiral recognition are required.
1. Peptide Synthesis
L-DiPhenylalanine is applied in peptide synthesis and peptide fragment construction where aromatic-rich residues are needed to tune folding propensity and intermolecular interactions. The amino acid backbone supports standard amide bond formation, while the phenyl rings on the side chain enable incorporation into longer sequences that require hydrophobic contacts and π-stacking. Protection-group strategies can be used to manage the amino and carboxyl functionalities during stepwise coupling, including N-protection to control chemoselectivity and C-terminal activation for sequential elongation. L-DiPhenylalanine-derived fragments can be used to generate peptide analogs and peptidomimetic scaffolds that retain stereochemical integrity through protected amino acid intermediate handling.
2. Peptidomimetics And SAR
L-DiPhenylalanine is utilized in peptidomimetics and structure-activity relationship studies where aromatic side-chain presentation and defined stereochemistry are central to molecular recognition. The compound's carboxyl and amino functionalities allow conversion into amide-linked analogs, while the two phenyl rings can be leveraged to modulate binding pocket hydrophobicity and conformational bias. Derivatization at the amino acid termini enables systematic variation of N- or C-terminal substituents, supporting SAR workflows that probe how aromatic spacing and stereochemical configuration affect physicochemical properties. L-DiPhenylalanine therefore serves as a chiral, aromatic-rich intermediate for generating libraries of peptide-like structures and for preparing defined fragments used in comparative binding and stability assessments.
3. Chemical Biology Labeling
L-DiPhenylalanine is suitable for chemical biology and biomolecule labeling workflows that require chiral, aromatic handles for conjugation and downstream detection. The amino acid functional groups can be converted into activated derivatives for coupling to amine- or carboxyl-reactive biomolecule scaffolds, while the phenyl rings contribute to fluorescence-sensitive environments or to controlled hydrophobic partitioning in conjugates. Protection and deprotection strategies allow selective functional group exposure, enabling orthogonal conjugation schemes when multiple reactive sites are present. L-DiPhenylalanine can be incorporated into labeled peptides or used as a chiral intermediate for preparing conjugation-ready aromatic amino acid derivatives used in biochemical research.
4. Protein Engineering Scaffolds
L-DiPhenylalanine is applied in protein engineering and scaffold design where aromatic residues influence local structure, stability, and interaction networks. The defined stereochemistry of the amino acid framework supports incorporation into engineered peptide segments, while the phenyl side chains provide tunable hydrophobic and π-interaction motifs that can affect helix propensity and binding interfaces. Terminal functionalization strategies enable attachment to linkers, tags, or crosslinkers, supporting controlled modification of protein fragments or peptide domains. L-DiPhenylalanine-based constructs can be used to generate defined chiral segments for studying structure-function relationships in engineered biomolecular systems.
5. Process Chemistry Intermediate
L-DiPhenylalanine is employed as a chiral aromatic amino acid intermediate in fine chemical synthesis and process chemistry where reproducible stereochemical outcomes and functional group compatibility are required. The amino acid backbone supports conversion into protected amino acid derivatives and activated coupling forms, supporting scalable manufacturing routes that rely on predictable chemoselectivity between N-protection and carboxyl activation. The aromatic-rich side chain can be used to design downstream intermediates for peptide building blocks, peptidomimetic fragments, and aromatic-functional materials precursors. L-DiPhenylalanine thus functions as a practical input for industrial intermediate preparation and for producing stereodefined aromatic amino acid derivatives used in applied chemical manufacturing.
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