Fmoc-3-Methy-D-Phenylalanine is a protected, non-natural amino acid derivative in which a phenylalanine scaffold bears a 3-methyl substitution on the aromatic ring and the amino acid is provided as the Fmoc-protected form. The molecule contains an Fmoc carbamate protecting the α-amino group and a free carboxylic acid functionality, with the D stereochemical configuration indicated by the product name and a hydrophobic benzyl-like side chain that presents a substituted phenyl ring. In peptide chemistry, it is employed as a stepwise building block for introducing the 3-methyl-D-phenylalanine residue into peptides or peptide-related intermediates while the Fmoc group helps control chemoselectivity during sequential coupling and deprotection steps.
CAT No: CP15707
Fmoc-3-Methy-D-Phenylalanine is an Fmoc-protected, chiral amino acid derivative in which the stereogenic center corresponds to the D-configuration and the side chain bears a 3-methyl substituted phenyl group. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group on the amino functionality and a free carboxylate or carboxylic acid handle depending on the supplied form, enabling controlled peptide coupling chemistry. The aromatic side chain provides a hydrophobic, π-interacting motif, while the benzylic substitution at the 3-position can influence conformational preferences and steric profile during amide bond formation and subsequent peptide folding. The combination of an Fmoc carbamate and a D-amino acid stereocenter makes the compound a useful chiral intermediate for protected amino acid synthesis and downstream peptide building block preparation.
1. Peptide Synthesis
Fmoc-3-Methy-D-Phenylalanine is applied in solid-phase peptide synthesis and related protected amino acid workflows where Fmoc deprotection and subsequent amide bond formation are central steps. The Fmoc-protected amine and the carboxyl functionality support standard peptide coupling strategies, while the D-stereochemistry provides stereochemical control for generating D-residue-containing sequences and for tuning backbone recognition. The 3-methyl substituted phenyl side chain can participate in hydrophobic packing and aromatic interactions that affect peptide secondary structure and stability. Incorporation into peptide building blocks enables preparation of D-amino acid peptides for mechanistic studies, scaffold diversification, and structure-activity relationship investigations.
2. Peptidomimetics And SAR
Fmoc-3-Methy-D-Phenylalanine is suitable for peptidomimetic construction in medicinal chemistry programs focused on structure-activity relationship studies and fragment-based molecular design. The D-configuration and aromatic side chain substitution pattern can modulate conformational bias, receptor contact geometry, and proteolytic resistance when embedded into peptide-like scaffolds. The Fmoc-protected amino acid format supports sequential assembly into analog libraries, including position-specific replacement of L-phenylalanine residues with a D-variant. Downstream derivatives can be generated by converting the peptide context into constrained peptidomimetics, enabling systematic SAR mapping of aromatic substitution effects.
3. Chemical Biology Labeling
Fmoc-3-Methy-D-Phenylalanine can be used in chemical biology for building labeled peptides and conjugatable biomolecule fragments where aromatic side-chain chemistry and stereochemical fidelity matter. The protected amino acid nature allows incorporation into peptide tags that later undergo side-chain or terminal functionalization depending on the chosen labeling strategy. The D-amino acid residue can be leveraged to improve stability of peptide probes against enzymatic degradation during assay timelines, while the substituted phenyl ring provides a defined hydrophobic and π-interaction surface for molecular recognition. The resulting D-residue-containing labeled constructs can serve as tools for studying binding interfaces, trafficking pathways, or protein-ligand interactions in controlled experimental systems.
4. Pharmaceutical Intermediate Preparation
Fmoc-3-Methy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and specialty fine chemical synthesis where Fmoc-protected chiral amino acids serve as manufacturing inputs for peptide-derived intermediates. The Fmoc carbamate protects the amine during synthetic sequence design, while the D-chiral center and substituted aromatic side chain preserve the stereochemical and structural information required for consistent downstream coupling. The carboxyl functionality enables conversion into activated derivatives or direct peptide coupling intermediates in a controlled process chemistry context. Manufactured peptide building blocks derived from this intermediate can be used for producing research-grade peptide candidates, process development materials, and analytical reference compounds.
5. Protein Engineering
Fmoc-3-Methy-D-Phenylalanine supports protein engineering and recombinant protein design workflows that incorporate noncanonical residues through peptide or fragment synthesis routes. The D-configuration provides a stereochemical handle for introducing backbone inversion at a defined position, which can influence local structure, protease susceptibility, and binding-site geometry in engineered constructs. The 3-methyl substituted phenyl side chain contributes a tunable hydrophobic volume and aromatic substitution pattern that can be exploited to adjust packing interactions within designed protein interfaces. The Fmoc-protected form facilitates stepwise assembly of D-containing segments that can be used as building blocks for larger biomolecular constructs and structure-function studies.
6. Analytical Research Standards
Fmoc-3-Methy-D-Phenylalanine is applicable in analytical research for generating D-residue-containing peptide standards and method development materials used in LC-MS, CE, and chromatographic peptide profiling. The protected amino acid structure enables preparation of defined sequences with known stereochemistry, allowing unambiguous discrimination between D- and L-containing analogs during analytical method validation. The aromatic 3-methyl phenyl side chain provides characteristic fragmentation and retention behavior that can improve detectability and identification in complex matrices. Use of this chiral building block in standard synthesis supports accurate quantitation, impurity mapping, and stereochemical verification for amino acid derivative and peptide manufacturing-related investigations.
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