Fmoc-beta,beta-diphenyl-Ala-OH is a protected, non-natural amino acid derivative in which the amino acid backbone corresponds to alanine bearing a β,β-diphenyl substitution on the side chain, classifying it as a bulky, conformationally restricted amino acid analogue for peptide-related synthesis. The molecule contains a free carboxylic acid (-COOH) and a primary amino group that is masked as an Fmoc carbamate, while the β,β-diphenyl motif provides two phenyl rings that increase hydrophobic character and steric bulk relative to standard alanine; stereochemistry is not specified in the name. In synthetic and chemical biology workflows, it is employed as an Fmoc-protected building block to introduce the β,β-diphenyl alanine unit into peptides or peptide mimetics, supporting structure-activity studies and the preparation of labeled or modified peptide frameworks through stepwise assembly.
CAT No: CP26716
CAS No:201484-50-6
Synonyms/Alias:201484-50-6;Fmoc-L-3,3-Diphenylalanine;Fmoc-3,3-diphenyl-L-alanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3,3-diphenylpropanoic acid;Fmoc-beta-phenyl-Phe-OH;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,3-diphenylpropanoic acid;Fmoc-|A-phenyl-Phe-OH;MFCD00672337;L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-beta-phenyl-;Fmoc-3,3-diphenyl-L-alaine;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3,3-diphenylpropanoic acid;Fmoc-3,3-diphenyl-D-alaine;Fmoc-Dph-OH;Fmoc-,-diphenyl-Ala-OH;Fmoc-(S)-2-Amino-3,3-diphenylpropanoic acid;SCHEMBL119505;DTXSID40942192;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3,3-diphenylpropanoic acid;AKOS025117411;AC-9896;CS-W011553;DS-8285;HY-W010837;PD196739;DB-038110;Fmoc-L-3,3-diphenylalanine (Fmoc-L-Dip-OH);Fmoc-beta-phenyl-Phe-OH, >=98.0% (HPLC);H10955;Fmoc-Dip-OH;Fmoc--phenyl-Phe-OH;Fmoc-3,3-diphenyl-L-alanine;N-{[(9H-Fluoren-9-yl)methoxy](hydroxy)methylidene}-beta-phenylphenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3,3-diphenylpropanoicacid;621-000-2;
Fmoc-beta,beta-diphenyl-Ala-OH is an Fmoc-protected, chiral amino acid derivative featuring an alanine backbone in which the beta carbon bears two phenyl substituents, creating a sterically congested, conformationally biased side chain. The molecule contains a free carboxylic acid for C-terminal engagement and an Fmoc carbamate on the amino function for orthogonal N-protection during peptide assembly. The stereogenic center at the alpha position is preserved, enabling stereochemically defined peptide construction and downstream structure-function studies. The diphenyl-substituted beta region introduces hydrophobic aromatic character and can participate in π-stacking and conformational restriction, while the carboxyl group supports standard coupling chemistry and further derivatization to industrially relevant intermediates.
1. Peptide Synthesis
Fmoc-beta,beta-diphenyl-Ala-OH is used as an Fmoc-based peptide building block for solid-phase peptide synthesis where the Fmoc carbamate enables controlled N-deprotection and the free carboxylic acid supports amide bond formation. The beta,beta-diphenyl substitution increases steric bulk near the coupling site, making the residue compatible with peptide coupling strategies designed for hindered amino acids and enabling stereochemically defined incorporation at the alpha center. The aromatic-rich side chain can be leveraged to modulate local folding propensity and enhance hydrophobic contacts in peptide scaffolds. The resulting peptides can be used as research-grade materials for mapping sequence effects, generating peptidomimetic analogs, and producing defined intermediates for further functionalization in amino acid chemistry workflows.
2. Peptidomimetics And SAR
Fmoc-beta,beta-diphenyl-Ala-OH serves in peptidomimetic construction and structure-activity relationship studies by providing a conformationally restricted, hydrophobic aromatic side chain that can replace native residues with defined steric and electronic properties. The stereogenic alpha carbon and the rigid beta,beta-diphenyl motif support the synthesis of analog series where side-chain geometry is systematically varied through protected amino acid selection and subsequent derivatization. The free carboxyl group and Fmoc-protected amine allow incorporation into larger scaffolds followed by selective transformations such as esterification, amidation, or orthogonal functional group installation. Downstream products include SAR-focused peptide analog libraries and chemically defined fragments suitable for medicinal chemistry exploration and comparative binding studies in biochemical research.
3. Side-Chain Functionalization
Fmoc-beta,beta-diphenyl-Ala-OH is suitable for side-chain functionalization strategies in synthetic organic chemistry where the diphenyl-substituted beta carbon provides an aromatic handle for subsequent derivatization while maintaining the amino acid stereochemistry. The Fmoc group provides orthogonal protection during early-stage modifications, allowing the residue to be carried through transformations that target aromatic rings or enable linker installation after peptide assembly. The presence of a free carboxylic acid supports conversion to activated esters or amide-forming derivatives, enabling downstream attachment to tags, linkers, or polymerizable units. The resulting functionalized amino acid derivatives can be employed to generate labeled probes, conjugation-ready intermediates, and material-building blocks derived from amino acid chemistry.
4. Chemical Biology Probes
Fmoc-beta,beta-diphenyl-Ala-OH is applied in chemical biology workflows for constructing peptide-based probes where hydrophobic, aromatic side-chain character can influence membrane association, target engagement, or binding-site residence time in assay systems. The Fmoc-protected amine supports incorporation into probe peptides with controlled N-terminus chemistry, while the stereodefined alpha center helps maintain predictable structure in binding studies. The beta,beta-diphenyl motif can function as a conformational constraint that improves interpretability of structure-dependent labeling experiments and supports generation of analogs for comparative analysis. Downstream use includes producing probe peptides and chemically defined conjugation intermediates that can be further modified for imaging, pull-down reagents, or affinity-based detection formats.
5. Pharmaceutical Intermediate Preparation
Fmoc-beta,beta-diphenyl-Ala-OH can be integrated into process chemistry and fine chemical synthesis routes for producing stereodefined amino acid intermediates used in peptide-derived active ingredient manufacturing. The orthogonal Fmoc protection strategy supports scalable peptide coupling sequences where N-protection and deprotection steps are compatible with industrially relevant solid-phase or solution-phase processing. The free carboxylic acid enables conversion to activated forms for controlled downstream assembly into larger intermediates, while the bulky aromatic side chain can be used to tune solubility and solid-state properties of intermediate peptides. The compound therefore functions as a chiral building block for manufacturing intermediate preparation, including the generation of defined peptidomimetic precursors and stereochemically consistent fragments for downstream synthesis.
6. Analytical Research Standards
Fmoc-beta,beta-diphenyl-Ala-OH is suitable for analytical research and method development where defined stereochemistry and a distinctive aromatic-rich side chain improve detectability in chromatographic and mass spectrometric workflows. The Fmoc group and free carboxylic acid provide clear chemical signatures that can support calibration standards, peptide fragment standards, and reference materials for monitoring peptide coupling efficiency or deprotection completeness in research settings. The beta,beta-diphenyl substitution yields strong hydrophobic retention behavior and characteristic fragmentation patterns that can aid identification of residue incorporation in complex mixtures. Downstream applications include supporting impurity profiling, identity verification of peptide intermediates, and construction of analytical panels for amino acid derivative characterization in biochemical research and industrial quality workflows.
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