Cbz-2,3-Difluoro-L-Phenylalanine is a Cbz-protected, fluorinated amino acid derivative in which the phenylalanine side chain is substituted with two fluorine atoms at the 2 and 3 positions of the aromatic ring, while the α-amino acid backbone retains the amino acid framework. The molecule contains a free carboxylic acid and a carbamate-protected α-amino group (Cbz), with the aromatic difluoro substitution altering side-chain electronics and steric profile relative to unsubstituted phenylalanine; the name specifies the L stereochemical configuration at the α-carbon. As a protected amino acid building block, it is employed in peptide synthesis and related structure-activity or labeling studies where incorporation of a difluorophenylalanine residue and controlled chemoselectivity of the amino functionality are required.
CAT No: CP12608
Cbz-2,3-Difluoro-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing two fluorine atoms at the 2- and 3-positions of the amino acid side of the backbone (α,β-difluoro substitution). The molecule contains a benzyloxycarbonyl (Cbz) carbamate that masks the stereogenic amino functionality while preserving a chiral, fluorinated carbon framework that can influence conformational preferences and peptide bond geometry. The difluoro substitution pattern introduces strong inductive effects and distinct electrophilic/steric behavior at the backbone, while the phenyl side chain supports hydrophobic and aromatic recognition interactions in peptide-like scaffolds. The compound is therefore positioned as a stereochemically defined, protected amino acid building block and chiral intermediate for preparing fluorinated peptide analogs and difluorinated amino acid derivatives suitable for downstream synthetic elaboration.
1. Peptide Synthesis
Cbz-2,3-Difluoro-L-Phenylalanine is used in peptide coupling chemistry to construct fluorinated peptide building blocks with backbone-difluoro substitution. The Cbz-protected amine supports standard peptide bond formation after deprotection or orthogonal activation, while the L-configuration provides defined stereochemical control at the α-center. The two fluorine atoms at the 2,3-positions can be retained through coupling to generate peptide analogs that probe how altered backbone electronics and steric profiles affect amide conformations. Fluorinated residues prepared from this chiral amino acid derivative can be incorporated into linear peptides and protected peptide fragments for structure-activity relationship studies and synthetic methodology development.
2. Peptidomimetics And SAR
Cbz-2,3-Difluoro-L-Phenylalanine is applied in peptidomimetic design where backbone fluorination is leveraged to modulate conformational bias and hydrogen-bonding patterns. The phenylalanine side chain and the difluoro-substituted backbone together enable incorporation into molecular scaffolds that mimic proteinogenic spacing while altering local polarity and dipole alignment. The Cbz carbamate enables controlled handling during sequential assembly, allowing orthogonal protection strategies when generating multi-residue analogs. Difluorinated peptide analogs derived from this building block can then be used in SAR studies as chemically defined probes for binding-site tolerance to fluorinated amino acid incorporation.
3. Protected Amino Acid Chemistry
Cbz-2,3-Difluoro-L-Phenylalanine serves as a chiral protected amino acid intermediate for synthesis planning that requires an N-protected difluoro amino acid platform. The Cbz group provides a removable protecting strategy compatible with common hydrogenolysis conditions, enabling stepwise deprotection to reveal the amine for subsequent coupling or derivatization. The fluorinated backbone can participate in downstream functional group transformations while maintaining stereochemical integrity of the L-center, supporting the preparation of additional fluorinated derivatives such as activated esters, amides, or side-chain-modified analogs. This makes the compound suitable for generating libraries of protected intermediates used in fine chemical synthesis and peptide building block preparation.
4. Chemical Biology Probes
Cbz-2,3-Difluoro-L-Phenylalanine is utilized to generate chemically defined fluorinated residues for chemical biology research tools that require stable backbone analogs. The difluoro substitution pattern can be exploited to tune metabolic stability and alter local electronic properties of peptide-like structures used as probes. The protected amino acid format supports incorporation into labeled or functionalized peptide constructs through peptide coupling chemistry, including assembly of fragments that later undergo selective deprotection and conjugation. Fluorinated analogs prepared from this compound can function as mechanistic probes in studies of biomolecular recognition, backbone-dependent binding, and enzyme-substrate specificity where stereodefined amino acid incorporation is required.
5. Pharmaceutical Intermediate Preparation
Cbz-2,3-Difluoro-L-Phenylalanine is relevant to pharmaceutical intermediate preparation for manufacturing routes that target fluorinated amino acid derivatives and peptide-like intermediates. The N-Cbz protection state provides a controllable handle for protecting-group management during multi-step synthesis, while the difluoro backbone offers a structurally defined motif used in medicinal chemistry programs. The phenylalanine side chain supports conversion into peptide fragments or further functionalization steps that can be integrated into process chemistry workflows. Downstream intermediates derived from this compound can be used to supply fluorinated building blocks for drug discovery chemistry and for the production of defined peptidomimetic candidates at the intermediate stage.
6. Process Chemistry for Fluorinated Building Blocks
Cbz-2,3-Difluoro-L-Phenylalanine is suitable for process chemistry applications focused on scalable synthesis of fluorinated chiral amino acid building blocks. The Cbz carbamate offers a robust protecting group for handling and purification during manufacturing of protected amino acid derivatives, and its deprotection strategy can be aligned with orthogonal protection schemes in peptide fragment production. The stereochemically defined L-configuration and the geminally fluorinated backbone motif enable reproducible construction of difluorinated residues that can be consistently incorporated into peptide coupling sequences. Industrially oriented use of this amino acid intermediate supports specialty chemical production where fluorinated chiral intermediates are required for fine chemical synthesis, peptidomimetic manufacturing, and downstream scaffold generation.
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