Fmoc-2,3-Dimethy-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino acid backbone bears an N-(9H-fluoren-9-ylmethoxycarbonyl) (Fmoc) protecting group and a D-configuration at the α-carbon, with a phenylalanine-like aromatic side chain substituted by methyl groups at the 2 and 3 positions. The molecule contains a free carboxylic acid functional group and a sterically modified, hydrophobic side chain, while the Fmoc carbamate masks the α-amino group to control chemoselectivity during stepwise assembly. It is used as a building block for peptide synthesis and structure-activity studies where incorporation of a sterically constrained, dimethyl-substituted phenylalanine analogue helps probe effects of side-chain shape and hydrophobicity on peptide properties.
CAT No: CP13807
Fmoc-2,3-Dimethy-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative bearing two methyl substituents at the 2- and 3-positions relative to the amino acid backbone, creating a sterically defined, chiral, quaternary-like side environment around the alpha-carbon region. The molecule contains the fluorenylmethoxycarbonyl (Fmoc) group on nitrogen, a carboxylate-protected functionality suitable for peptide coupling workflows, and a pendant phenyl ring that supports hydrophobic and aromatic interactions in peptide and peptidomimetic contexts. The D-configuration and the geminal/adjacent methyl pattern influence stereochemical outcomes during amide bond formation and downstream transformations, while the Fmoc carbamate enables orthogonal protection strategies compatible with standard base-mediated deprotection. The resulting amino acid building block functions as a chiral synthetic intermediate for constructing sterically constrained peptide analogs and for preparing functionalized derivatives through controlled manipulation of the protected amino acid framework.
1. Peptide Synthesis
Fmoc-2,3-Dimethy-D-Phenylalanine is applied in solid-phase and solution-phase peptide synthesis where Fmoc protection supports stepwise assembly of peptide building blocks. The presence of the Fmoc carbamate and the amino acid backbone enables peptide coupling via standard amide-forming chemistries after Fmoc removal, while the D-stereochemistry and the 2,3-dimethyl substitution pattern impose conformational bias and steric shielding near the growing peptide chain. The phenyl side chain provides an aromatic handle for hydrophobic packing and can be used to tune local secondary structure propensity in peptide analog libraries. The compound can therefore serve as a chiral residue for constructing sterically constrained sequences and for generating peptide building block sets used in structure-activity relationship studies and peptide science workflows.
2. Peptidomimetics And SAR
Fmoc-2,3-Dimethy-D-Phenylalanine is utilized in peptidomimetic construction and SAR studies where the combination of D-configuration, alpha-region methyl substitution, and aromatic side chain supports mimicry of constrained proteinogenic motifs. The 2,3-dimethyl pattern can modulate backbone torsion angles and reduce conformational freedom, while the phenyl ring contributes to aromatic interaction networks that are often central to binding-site recognition. Fmoc protection allows incorporation of this residue into larger scaffolds, including cyclic or stapled analogs, by maintaining compatibility with iterative coupling and orthogonal deprotection schemes. The resulting D-amino acid-containing analogs can be used as chemically defined probes to map structure-function relationships and to generate downstream derivative series for medicinal chemistry optimization.
3. Side-Chain Functionalization
Fmoc-2,3-Dimethy-D-Phenylalanine is suitable for amino acid derivatization and side-chain functionalization strategies that leverage the aromatic phenyl group and the sterically tuned alpha-substitution environment. The protected amino acid framework allows selective transformations after incorporation into intermediates or after controlled deprotection, enabling conversion of the phenyl ring to functional analogs such as substituted aryl derivatives or handles for subsequent coupling reactions. The D-stereocenter and adjacent methyl substituents can influence regioselectivity and reactivity during electrophilic aromatic substitution, cross-coupling, or oxidation/reduction sequences applied to aryl-functionalized derivatives. The compound thus supports the generation of functionalized amino acid derivatives and intermediate scaffolds used in synthetic organic chemistry and in the assembly of labeled or conjugatable peptidomimetic fragments.
4. Chemical Biology Probes
Fmoc-2,3-Dimethy-D-Phenylalanine is employed in chemical biology research to introduce a defined D-amino acid residue into peptide-based probes used for target engagement studies and biomolecular interaction mapping. The Fmoc group supports controlled incorporation into probe sequences, while the D-configuration and sterically hindered 2,3-dimethyl region can improve resistance to proteolysis and maintain specific conformations within the probe scaffold. The phenyl side chain provides a hydrophobic and aromatic moiety that can participate in binding-site contacts, supporting probe design where steric and electronic effects are tuned at the residue level. The resulting labeled or conjugatable peptide analogs can be used as biochemical research intermediates for developing molecular probes and for generating chemically consistent reagent sets for interaction studies.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-2,3-Dimethy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and process chemistry for producing non-natural amino acid residues used in peptide and peptidomimetic manufacturing routes. The Fmoc-protected form provides a stable, isolable chiral building block that can be handled as a defined input material for controlled deprotection and coupling steps during scale-up-oriented synthesis planning. The stereochemical integrity of the D-amino acid and the sterically constrained 2,3-dimethyl substitution pattern support reproducible incorporation into final peptide intermediates, reducing variability associated with stereochemical scrambling in downstream steps. The compound can therefore function as a chiral process intermediate for specialty chemical production where protected amino acid synthesis, protected residue handling, and robust peptide coupling compatibility are key to manufacturing workflows.
6. Analytical Standards for Chiral Chemistry
Fmoc-2,3-Dimethy-D-Phenylalanine is applicable to analytical research as a chiral amino acid reference material and method development standard for LC/UPLC and chiral separation workflows. The Fmoc group provides a strong chromophore and mass spectrometric signal, facilitating detection and quantitation during monitoring of deprotection, coupling, and residue incorporation in peptide synthesis streams. The D-stereochemistry combined with the 2,3-dimethyl substitution pattern yields a distinct retention and fragmentation profile, supporting identification of the correct stereochemical and structural variant in complex peptide mixtures. The compound can be employed to validate analytical methods for protected amino acid intermediates, peptide building block quality control, and characterization of D-amino acid-containing synthetic products used in applied peptide chemistry.
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