Fmoc-2,4-Dimethy-D-Phenylalanine is an Fmoc-protected, D-configured phenylalanine derivative bearing additional methyl substituents at the 2- and 4-positions of the aromatic ring, placing it in the class of non-natural, sterically and electronically modified amino acids used for peptide building blocks. The molecule contains a free carboxyl group and an Fmoc carbamate on the amino functionality, while the dimethylated phenyl side chain provides hydrophobic character and altered aromatic substitution patterns that can influence peptide conformation and intermolecular contacts. As a protected amino acid intermediate, it is employed in peptide synthesis workflows, including solid-phase peptide synthesis, where the Fmoc group supports stepwise coupling while the modified aromatic side chain enables structure-activity and structure-property studies of substituted phenylalanine analogues.
CAT No: CP13907
Fmoc-2,4-Dimethy-D-Phenylalanine is an Fmoc-protected, D-configured phenylalanine derivative featuring a chiral α-carbon and a substituted aromatic side chain with two methyl substituents at the 2- and 4-positions relative to the benzylic framework. The molecule contains the fluorenylmethoxycarbonyl (Fmoc) carbamate on the amino group, a carboxylate functionality typically present as the protected acid form suitable for peptide coupling workflows, and a hydrophobic, sterically biased side chain that can influence conformation and packing in peptide backbones. The D-stereochemistry provides controlled inversion relative to L-amino acid analogs, enabling stereochemically defined incorporation into peptides and peptidomimetics. The aromatic ring substitution pattern can participate in π-π and hydrophobic interactions while also modulating electrophilic aromatic reactivity and downstream derivatization options through selective functional group transformations.
1. Peptide Synthesis
Fmoc-2,4-Dimethy-D-Phenylalanine is used in solid-phase peptide synthesis and related protected amino acid chemistry to introduce a D-amino acid residue with an Fmoc-protected amine compatible with standard base-mediated Fmoc removal. The chiral α-center and the carboxyl functionality support peptide coupling chemistry, while the substituted phenyl side chain provides steric and electronic control over local peptide conformation, aggregation propensity, and side-chain orientation. The Fmoc carbamate strategy enables sequential N-terminal protection during chain assembly and clean deprotection cycles that preserve stereochemical integrity of the D-configured center. The resulting D-aryl substituted peptides can serve as research-grade building blocks for studying sequence-dependent structure and stability in amino acid and peptide science.
2. Peptidomimetics And SAR
Fmoc-2,4-Dimethy-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship studies where incorporation of D-amino acid stereochemistry and bulky, methyl-substituted aromatic side chains can tune target binding and proteolytic stability profiles. The aromatic ring bearing 2,4-dimethyl substitution can modulate hydrophobic contact surfaces and conformational preferences, supporting rational design of analog series for SAR investigations. The Fmoc-protected amino acid format allows systematic substitution at a defined position within peptide scaffolds, facilitating comparative synthesis of stereochemically matched analogs. Downstream, the D-phenylalanine residue can be carried into larger fragment libraries and SAR panels used in medicinal chemistry workflows focused on amino acid derivatization and peptide analog optimization.
3. Protein Engineering
Fmoc-2,4-Dimethy-D-Phenylalanine is suitable for protein engineering efforts that rely on chemically defined peptide segments, including semisynthetic proteins and engineered peptide domains where noncanonical amino acid content is required. The D-configuration and hydrophobic substituted phenyl side chain can influence secondary structure propensity and local folding behavior when incorporated into peptide regions used to model or modulate protein interfaces. The protected amino acid nature supports stepwise assembly of defined sequences that can later be converted into ligation-ready fragments or used as reference materials for structure-function studies. The compound thus functions as a stereochemically controlled chiral building block for generating amino acid-modified peptide constructs relevant to protein science and molecular recognition research.
4. Bioconjugation Chemistry
Fmoc-2,4-Dimethy-D-Phenylalanine is employed in bioconjugation chemistry to create peptide handles bearing a defined D-amino acid motif and a hydrophobic aryl side chain for controlled conjugate architecture. The Fmoc-protected amino group enables incorporation into peptide sequences that can be further functionalized at other positions, while the substituted aromatic ring can contribute to conjugate stability through hydrophobic and π-interaction effects during labeling and purification. The D-stereocenter can also support resistance to enzymatic cleavage in conjugate contexts where protease stability is a design variable. The resulting amino acid-based intermediates can be used to generate labeled peptides, affinity probes, or conjugation scaffolds for chemical biology research and downstream biomolecule modification.
5. Process Chemistry Intermediate
Fmoc-2,4-Dimethy-D-Phenylalanine is relevant to process chemistry and specialty chemical production as a chiral, protected amino acid intermediate that supports scalable peptide building block preparation. The Fmoc protecting group provides a robust N-protection handle for manufacturing workflows that require predictable deprotection behavior and controlled coupling compatibility, while the D-stereochemistry ensures stereochemical fidelity across batch syntheses. The substituted phenyl side chain increases hydrophobic character, which can affect solubility management and purification strategy during intermediate handling and peptide assembly. The compound can therefore serve as a defined stereochemical input for producing D-amino acid-containing peptides and peptidomimetic intermediates used in fine chemical synthesis and industrial peptide supply chains.
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