Fmoc-3,4-Dimethy-D-Phenylalanine is an Fmoc-protected, non-natural amino acid derivative in which the phenylalanine backbone bears a 3,4-dimethyl-substituted phenyl side chain and the amino acid nitrogen is masked as an N-(9H-fluoren-9-ylmethoxycarbonyl) (Fmoc) carbamate. The molecule contains a free carboxyl functional group and an Fmoc-protected amino group, with the "D" stereochemical designation indicating the D-configuration at the alpha carbon, while the aromatic side chain provides a hydrophobic, substituted phenyl functionality for structure-property studies and peptide incorporation. In synthetic peptide chemistry and chemical biology workflows, this protected analogue is used as a building block to introduce the sterically and electronically modified dimethylphenylalanine residue during stepwise assembly of peptides or peptide-related intermediates.
CAT No: CP14207
Fmoc-3,4-Dimethy-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative bearing two methyl substituents at the 3,4-positions of the aromatic ring, forming a sterically differentiated, chiral amino acid building block. The molecule contains a carbamate-protected α-amino group (Fmoc), a carboxylate functionality suitable for peptide coupling after activation or conversion to an appropriate acid form, and a substituted benzyl side chain that can modulate hydrophobicity and aromatic packing. The D-configuration at the α-carbon enables stereochemically defined incorporation into peptides and peptidomimetics, supporting control over backbone conformation and protease resistance patterns. The aryl ring's methyl groups influence electronic density and reactivity toward electrophilic aromatic substitution and downstream derivatization, while the Fmoc group provides a standard protection strategy compatible with solid-phase workflows.
1. Peptide Synthesis
Fmoc-3,4-Dimethy-D-Phenylalanine is used as a protected amino acid building block for peptide coupling chemistry in automated and manual synthesis platforms. The Fmoc carbamate protects the α-amino functionality during chain assembly and can be removed under base conditions to expose the amino group for subsequent coupling cycles. The D-stereocenter and the 3,4-dimethyl-substituted phenyl side chain provide stereodefined incorporation and aromatic hydrophobic character, which can be leveraged to tune folding propensity and side-chain packing in peptide sequences. The resulting D-amino acid residue can be incorporated into linear peptides and cyclic scaffolds, enabling preparation of peptide analogs for biochemical research and structure-activity relationship studies. The protected amino acid format also supports downstream purification and intermediate handling typical of peptide manufacturing workflows.
2. Peptidomimetics And SAR
Fmoc-3,4-Dimethy-D-Phenylalanine serves as a chiral residue for peptidomimetic construction and structure-activity relationship studies where aromatic side-chain modification is used to tune molecular recognition. The substituted phenyl ring with 3,4-dimethyl substitution provides a defined hydrophobic and steric profile that can be systematically compared across analog series, while the D-configuration at the α-carbon can alter backbone stereochemistry relative to L-analogues. Fmoc protection enables controlled assembly of analog libraries, and the amino acid's carboxyl group participates in amide bond formation to generate stable peptide-like linkages. The compound's structural features can be applied to create constrained or protease-resistant motifs for SAR mapping of binding interfaces and conformational preferences. Amino acid chemistry compatibility with standard coupling reagents makes it suitable for iterative synthesis of structure-defined analogs in medicinal chemistry programs.
3. Side-Chain Functionalization
Fmoc-3,4-Dimethy-D-Phenylalanine is suitable for side-chain functionalization strategies that start from an aromatic amino acid scaffold and proceed to diversified derivatives. The 3,4-dimethyl-substituted phenyl side chain can undergo electrophilic aromatic transformations or oxidative modifications that preserve the protected amino acid framework until peptide coupling is complete. The Fmoc-protected α-amino group and carboxyl functionality allow orthogonal timing of protection and deprotection, enabling selective conversion of the aromatic ring while maintaining the integrity of the amino acid stereocenter. The D-configuration provides stereochemical control over the backbone while aromatic derivatization can introduce new physicochemical properties such as altered polarity, polarizability, or handle introduction for further conjugation. Downstream, ring-modified D-phenylalanine residues can be used to generate fluorescent or affinity-tagged peptide analogs, or to prepare defined intermediates for broader synthetic organic chemistry campaigns.
4. Chemical Biology And Protein Engineering
Fmoc-3,4-Dimethy-D-Phenylalanine can be employed in chemical biology workflows that require incorporation of noncanonical D-amino acid residues into peptide probes or protein segments. The Fmoc-protected amino acid format supports stepwise assembly into peptide tags, enzyme substrates, or binding domains used for mechanistic studies, while the D-stereochemistry provides a handle for controlling stereochemical recognition by enzymes and binding proteins. The aromatic side chain with 3,4-dimethyl substitution can influence membrane association tendencies and hydrophobic contacts in biomolecular interfaces, supporting design of probes with defined aromatic character. The resulting D-amino acid-containing constructs can serve as tools for mapping interaction surfaces, evaluating substrate specificity, or probing conformational effects in engineered peptide systems. The compound's compatibility with standard peptide coupling chemistry makes it applicable to applied protein engineering and synthetic biomolecule design.
5. Pharmaceutical Intermediate Preparation
Fmoc-3,4-Dimethy-D-Phenylalanine is applicable as a chiral intermediate for pharmaceutical intermediate preparation and fine chemical synthesis where protected amino acid derivatives are required for controlled assembly of active or research-grade scaffolds. The Fmoc-protected α-amino group is a process-compatible protecting-group strategy that allows sequential manufacturing steps, including controlled deprotection and coupling to generate defined amide linkages. The D-configuration supports stereochemically consistent synthesis of peptide-like fragments used in medicinal chemistry and advanced intermediate generation, while the 3,4-dimethyl-substituted phenyl ring provides a stable aromatic motif for incorporation into larger molecules. The compound can be converted into downstream coupling-ready forms and used to build multi-step routes that require robust handling of chiral amino acid units. Industrial relevance is supported by the standardized protected amino acid format, enabling integration into peptide fragment synthesis and specialty chemical production supply chains.
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