Fmoc-2,4-Dimethy-L-Phenylalanine is an Fmoc-protected amino acid derivative in which the phenylalanine side chain bears two methyl substituents at the 2- and 4-positions, providing a substituted aromatic functionality for structure-activity and steric-constraint studies. The molecule contains a free carboxyl group and an Fmoc-protected amino group, with stereochemistry indicated as L at the α-carbon, and the aromatic side chain can participate in hydrophobic and π-interaction patterns during peptide formation. As a protected building block, it is used in peptide synthesis workflows to introduce the 2,4-dimethylphenylalanine residue with controlled chemoselectivity at the amino functionality while maintaining the α-carboxyl group for coupling to neighboring peptide segments.
CAT No: CP13906
Fmoc-2,4-Dimethy-L-Phenylalanine is an Fmoc-protected L-phenylalanine derivative bearing two additional methyl substituents at the 2- and 4-positions of the aromatic ring. The molecule contains a chiral α-carbon typical of amino acid building blocks, a benzylic side chain that preserves hydrophobic character, and an Fmoc carbamate that supports base-compatible peptide coupling workflows while limiting undesired amine reactivity. The aromatic ring's steric and electronic modulation from the ortho and para methyl groups can influence coupling outcomes, conformational preferences, and downstream derivatization chemistry. As a protected amino acid intermediate, it functions as a chiral, N-Fmoc amino acid suitable for incorporation into peptide sequences and for generating substituted phenylalanine analogs used in structure-focused synthesis and materials-oriented studies.
1. Peptide Synthesis
Fmoc-2,4-Dimethy-L-Phenylalanine is used in peptide building workflows where N-Fmoc protection enables controlled deprotection and subsequent amide bond formation. The retained L-configuration at the α-carbon and the aromatic side chain with 2,4-dimethyl substitution provide a defined stereochemical and steric environment that can be carried through iterative coupling cycles. The Fmoc carbamate can be removed under standard base conditions to expose the amino group for peptide coupling, while the aromatic methyl pattern can tune hydrophobic packing and local conformational effects in the growing chain. Peptide synthesis applications include preparation of substituted phenylalanine-containing peptides for biophysical characterization, SAR-oriented analog libraries, and peptide scaffold optimization.
2. Peptidomimetic Design
Fmoc-2,4-Dimethy-L-Phenylalanine supports peptidomimetic construction by supplying a chiral phenylalanine-like motif with a substituted aromatic ring that can modulate binding-site interactions. The α-amino acid backbone and carboxyl functionality (present as the activated coupling handle during synthesis) allow incorporation into peptide-like frameworks, while the 2,4-dimethyl substitution can influence π-π contacts, steric shielding, and hydrophobic surface area. Fmoc protection provides a practical handle for assembling analogs that later undergo side-chain functional group transformations or backbone modifications. Downstream use can include generating constrained or substituted peptide analogs for molecular recognition studies and fragment-to-lead optimization efforts.
3. Side-Chain Functionalization
Fmoc-2,4-Dimethy-L-Phenylalanine is applicable to side-chain functionalization strategies that exploit the substituted aromatic ring for further synthetic elaboration. The ortho and para methyl groups can direct regioselective electrophilic aromatic substitution, enabling access to additional aryl substituents after incorporation or during intermediate-stage derivatization. The Fmoc-protected amine allows selective chemistry at the aromatic ring and carboxyl-derived functionalities without premature amide formation, supporting stepwise synthesis of diversified phenylalanine analogs. Resulting derivatives may serve as intermediates for medicinal chemistry-style libraries, chemical biology probes with tuned hydrophobicity, and specialty chemical syntheses where substituted aromatic amino acid motifs are required.
4. Structure-Activity Relationship Studies
Fmoc-2,4-Dimethy-L-Phenylalanine is used in SAR studies where controlled variation of aromatic side-chain sterics and electronics is needed across peptide or peptidomimetic series. The L-stereocenter ensures consistent chiral presentation, while the 2,4-dimethyl phenyl ring can be used to systematically probe how steric bulk and hydrophobic character affect binding or stability proxies measured in vitro. Fmoc compatibility supports parallel synthesis of analog panels by enabling standardized coupling chemistry and reproducible incorporation into sequence-defined constructs. Downstream derivatives generated from these analogs can feed analytical comparisons, mechanistic investigations, and structure-informed optimization of amino acid-rich scaffolds.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,4-Dimethy-L-Phenylalanine serves as a chiral amino acid intermediate for manufacturing-oriented synthesis of substituted phenylalanine building blocks used in drug-development chemistry. The Fmoc-protected amine provides a protected functional group strategy that aligns with scalable peptide coupling routes, allowing controlled formation of amide linkages during intermediate assembly. The aromatic 2,4-dimethyl pattern can be carried into active pharmaceutical ingredient precursors or into process intermediates that require defined hydrophobic motifs and stereochemical integrity. Industrial utility includes preparation of research-grade peptide fragments, process intermediates for larger synthetic sequences, and fine chemical production of substituted amino acid derivatives compatible with downstream deprotection and conjugation steps.
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