Fmoc-alpha-Me-D-Phe(2-F)-OH is an Fmoc-protected, non-natural D-amino acid derivative in which the alpha carbon bears a methyl substituent and the side chain is a phenylalanine motif substituted with a fluorine at the 2-position. The molecule contains a carboxylic acid functional group and an Fmoc carbamate protecting group on the amino functionality, while the aromatic ring fluorination provides a strongly electron-withdrawing substituent that can influence hydrophobicity and conformational preferences in peptide contexts. In peptide chemistry and chemical biology, it is used as a protected building block for incorporating an alpha-methylated, 2-fluorinated phenylalanine analogue into peptides or peptide-like constructs for structure-activity studies, backbone modification mapping, and analytical method development requiring chemically defined fluorinated residues.
CAT No: CP25304
CAS No:1315449-93-4
Synonyms/Alias:(R)-N-Fmoc-alpha-Methyl-2-fluorophenylalanine
Chemical Name:(R)-N-alpha-(9-Fluorenylmethyloxycarbonyl)-C-alpha-methyl-2-fluorophenylalanine
Fmoc-alpha-Me-D-Phe(2-F)-OH is an Fmoc-protected, D-configured phenylalanine derivative bearing an alpha-methyl substituent and a 2-fluoro-substituted phenyl side chain. The molecule combines a stereodefined amino acid core with an aromatic fluorine handle, enabling controlled peptide coupling through the Fmoc-protected nitrogen and providing an additional site for electronic and steric modulation in downstream structure-activity relationship studies. The alpha-methyl stereocenter and the D-configuration support stereochemically consistent incorporation into peptide sequences and can influence conformational preferences and protease recognition. The carboxylic acid functionality remains available for amide bond formation, while the fluorinated aromatic ring can participate in selective derivatization, spectroscopic tracking, and medicinal chemistry-style fluorine effects.
1. Peptide Synthesis
Fmoc-alpha-Me-D-Phe(2-F)-OH is used as a protected amino acid building block for solid-phase peptide synthesis and solution-phase peptide coupling where Fmoc deprotection exposes the secondary amine for amide bond formation. The alpha-methyl substitution and D-phenylalanine stereochemistry can be leveraged to control backbone stereochemical outcomes and to introduce conformational constraints that may affect peptide folding and cleavage susceptibility. The carboxylic acid group supports standard peptide coupling strategies, while the 2-fluoro aromatic side chain provides a chemically stable motif for incorporation into fluorinated peptide analog libraries. The resulting fluorinated, alpha-methylated peptide products can be used as research-grade sequence variants for peptide science and for method development in peptide construction.
2. Peptidomimetics And SAR
Fmoc-alpha-Me-D-Phe(2-F)-OH is applied in peptidomimetic and structure-activity relationship workflows where fluorinated aromatic side chains and alpha-methylated backbones are used to tune binding interactions and metabolic stability proxies. The D-configuration and alpha-methyl group introduce stereochemical features that can alter hydrogen-bonding patterns and side-chain orientation compared with non-methylated analogs. The 2-fluoro substituent serves as an electronic modulator and a handle for physicochemical property tuning, supporting generation of fluorinated analog series for SAR studies. The compound's defined stereochemistry and protected amine enable reproducible incorporation into peptide-derived scaffolds used in medicinal chemistry-oriented research programs.
3. Chemical Biology Labeling
Fmoc-alpha-Me-D-Phe(2-F)-OH is suitable for chemical biology research that requires incorporation of fluorinated amino acid residues into peptides for analytical tracking and molecular recognition studies. The Fmoc-protected nitrogen supports controlled installation into peptide constructs, while the 2-fluoro phenyl ring can function as a spectroscopic tag in NMR-based monitoring and can be used to distinguish analogs within combinatorial peptide sets. The alpha-methylated, D-amino acid backbone can help generate stable peptide probes that resist certain enzymatic processing pathways, supporting downstream studies of biomolecular interactions. The carboxylic acid enables conversion into peptide amides that can be further elaborated into conjugatable or assay-compatible constructs.
4. Pharmaceutical Intermediate Preparation
Fmoc-alpha-Me-D-Phe(2-F)-OH is employed as a stereochemically defined intermediate for manufacturing-oriented synthesis of fluorinated peptide fragments and protected amino acid derivatives used in fine chemical production. The Fmoc group provides an industrially compatible protection strategy for nitrogen during sequential assembly, while the free carboxylic acid functionality enables conversion into activated derivatives for downstream fragment coupling. The alpha-methyl and D-stereocenters help ensure that the resulting peptide intermediates maintain the intended stereochemical identity through multi-step synthetic sequences. The 2-fluoro aromatic moiety supports preparation of fluorinated drug-like building blocks and peptide-based intermediates used in process chemistry routes for specialty chemical manufacturing.
5. Side-Chain Functionalization
Fmoc-alpha-Me-D-Phe(2-F)-OH is used in amino acid derivatization programs where the 2-fluoro substituent on the phenyl side chain enables subsequent functional group transformations after peptide assembly or during fragment elaboration. The aromatic fluorine can be retained to modulate lipophilicity and binding properties, or can serve as a reactive handle in strategies that introduce additional substituents on the aryl ring depending on the chosen synthetic plan. The alpha-methylated D-amino acid backbone provides a stereodefined scaffold that can be carried through to final functionalized analogs, supporting consistent SAR or material-related property tuning. Fmoc protection allows stepwise synthesis and controlled deprotection, enabling production of fluorinated side-chain variants for downstream chemical biology and synthetic organic chemistry applications.
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