Fmoc-2,6-Dimethy-D-Phenylalanine is a protected, non-proteinogenic amino acid derivative in which the phenylalanine backbone bears an N-(9H-fluoren-9-ylmethoxycarbonyl) (Fmoc) protecting group and a 2,6-dimethyl substitution on the aromatic side chain, with the D stereochemical form indicated by the product name. The molecule contains a free carboxyl group and a side chain that retains a hydrophobic, sterically hindered benzyl-like functionality, while the Fmoc carbamate masks the amino group to control chemoselectivity during stepwise peptide assembly. In synthesis and chemical biology workflows, this protected amino acid is employed as a building block for incorporating a sterically modified aromatic residue into peptides and for generating labeled or structurally constrained peptide analogues for structure-activity and binding studies.
CAT No: CP14107
Fmoc-2,6-Dimethy-D-Phenylalanine is a D-configured, Fmoc-protected amino acid bearing a phenylalanine-derived aromatic side chain substituted at the 2 and 6 positions with methyl groups. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group on the amino functionality and a free carboxyl group that can be converted into coupling-ready derivatives. The 2,6-dimethyl substitution increases steric shielding around the aromatic ring while preserving a hydrophobic, shape-defining side chain that can influence peptide secondary structure propensity and binding-site recognition. The defined stereochemistry at the α-carbon supports stereochemically controlled peptide coupling and downstream incorporation into D-amino acid sequences for stable, protease-resistant peptide analogs.
1. Peptide Synthesis
Fmoc-2,6-Dimethy-D-Phenylalanine is used in solid-phase peptide synthesis and related protected amino acid strategies where the Fmoc group enables orthogonal N-deprotection and controlled amide bond formation. The combination of the Fmoc-protected amine with a carboxylic acid functionality supports standard peptide coupling chemistry while maintaining the D-configuration at the stereogenic center. The bulky, 2,6-dimethyl-substituted phenyl side chain can modulate local sterics during chain assembly and can be leveraged to tune helix packing, turn formation, and hydrophobic contacts in peptide scaffolds. Incorporation of this D-amino acid building block supports construction of peptide libraries and sequence-defined analogs for structure-function studies and synthetic methodology development.
2. Peptidomimetics And SAR
Fmoc-2,6-Dimethy-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship studies where D-amino acid incorporation and aromatic side-chain sterics act as molecular design variables. The Fmoc-protected amino acid format supports rapid assembly of analog series in which the 2,6-dimethyl phenyl group provides a sterically constrained hydrophobic pharmacophore. The D stereochemistry can be used to probe stereochemical effects on target recognition, conformational stability, and resistance to enzymatic degradation without altering the core aromatic functionality. Downstream peptide analogs prepared from this building block can serve as SAR probes, enabling systematic evaluation of how aromatic substitution patterns and stereochemistry influence binding interactions.
3. Chiral Building Block Synthesis
Fmoc-2,6-Dimethy-D-Phenylalanine is utilized as a chiral amino acid intermediate for stereochemically defined synthesis of D-amino acid-containing fragments and protected derivatives. The α-chiral center and the Fmoc carbamate protecting group provide a stable handle for iterative protection, coupling, and selective deprotection workflows in fine chemical synthesis. The 2,6-dimethyl-substituted phenyl ring can act as a steric directing element in subsequent derivatization steps, including transformations that preserve the aromatic core while modifying other functional handles. This makes the compound suitable for preparing chiral peptide building blocks, fragment-based library members, and downstream intermediates that retain stereochemical integrity through multi-step manufacturing routes.
4. Chemical Biology Probes
Fmoc-2,6-Dimethy-D-Phenylalanine is suitable for chemical biology research where D-amino acid peptides are used to create stable probes for receptor mapping, binding-site characterization, and protein interaction studies. The Fmoc-protected amino acid enables incorporation into labeled or functionalized peptide constructs through controlled N-terminal chemistry and subsequent conjugation-ready peptide formation. The sterically shielded aromatic side chain can influence binding pocket accommodation and can help differentiate interactions driven by hydrophobic packing versus steric complementarity. Resulting D-peptide probes can be employed as sequence-defined tools for studying molecular recognition and for generating well-defined substrates or competitors in biochemical assays.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-2,6-Dimethy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and process chemistry for manufacturing peptide-like intermediates that require stereochemical control and robust protecting-group compatibility. The Fmoc group supports scalable orthogonal deprotection logic commonly used in peptide production workflows, while the carboxylic acid functionality enables conversion to activated coupling forms during intermediate fabrication. The D-amino acid stereochemistry and the sterically encumbered 2,6-dimethyl phenyl side chain can be leveraged to build metabolically stable peptide scaffolds used as upstream materials in drug discovery pipelines. This compound therefore functions as a defined chiral building block for producing peptide intermediates and peptidomimetic fragments under controlled synthetic sequences.
6. Side-Chain Functionalization Chemistry
Fmoc-2,6-Dimethy-D-Phenylalanine is applied in amino acid modification and side-chain functionalization strategies where the aromatic ring substitution pattern supports selective chemical design of hydrophobic and steric features. The Fmoc-protected amine allows the compound to be incorporated into peptide frameworks before side-chain-directed transformations, enabling late-stage functionalization of conjugation handles on the assembled scaffold. The 2,6-dimethyl substitution can reduce undesired electrophilic or oxidative side reactions on the aromatic ring during certain downstream steps, while still providing a stable hydrophobic motif for conjugate formation. Resulting functionalized D-peptide derivatives can be used for bioconjugation chemistry, analytical standard preparation, and generation of structure-defined materials that rely on controlled aromatic sterics and stereochemistry.
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