Cbz-3-Methoxy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a benzyl carbamate (Cbz) on the amino group and a 3-methoxy-substituted phenyl side chain, with the D stereochemical configuration specified in the name. The molecule contains a free carboxyl functional group and a protected α-amino functionality, and the aromatic ether side chain provides a methoxy substituent that can influence polarity and conformational preferences in peptide-like structures. In peptide chemistry and chemical biology, it functions as a protected building block for incorporating a 3-methoxy-phenylalanine residue into oligopeptides or labeled analogues, supporting stepwise coupling strategies that rely on temporary amine protection to control chemoselectivity.
CAT No: CP15409
Cbz-3-Methoxy-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) carbamate on the α-amino group and a 3-methoxy substituent on the aromatic side chain. The molecule presents a stereogenic center at the amino acid α-carbon, enabling stereochemically defined peptide incorporation and chiral intermediate use. The Cbz-protected amine and the aromatic methoxy group provide distinct reactivity handles: carbamate stability under many coupling conditions and controlled deprotection strategies, while the anisole functionality can participate in electrophilic aromatic substitution, oxidative transformations, or later functional group elaboration. As a protected amino acid derivative and chiral building block, it is well-suited for peptide coupling chemistry and downstream synthesis of aromatic side-chain modified analogs.
1. Peptide Synthesis
Cbz-3-Methoxy-D-Phenylalanine is applied in peptide building-block preparation for solid-phase or solution-phase peptide synthesis where a D-amino acid stereocenter is required. The Cbz-protected α-amine supports amide bond formation after activation of the corresponding carboxyl functionality, while the aromatic 3-methoxy side chain remains compatible with common coupling and protecting-group regimes. The chiral configuration at the α-carbon enables incorporation into peptide sequences to generate stereochemically defined D-phenylalanine motifs and to tune conformational preferences. The resulting D-aryl peptide fragments can be used to construct peptide analogs for mechanistic studies, peptidomimetic scaffolds, and structure-activity relationship investigations that depend on side-chain electronics and stereochemistry.
2. Peptidomimetics And SAR
Cbz-3-Methoxy-D-Phenylalanine is utilized in peptidomimetic construction and SAR studies where aromatic side-chain modulation and D-amino acid incorporation influence binding and stability. The 3-methoxy substituent on the phenyl ring provides an electron-donating handle that can affect aromatic interactions, hydrogen-bonding patterns, and metabolic stability trends in designed analogs. The Cbz carbamate allows controlled N-deprotection to reveal a reactive amine for subsequent derivatization or for continuation of peptide assembly. Downstream synthetic use includes generating libraries of aromatic-substituted D-phenylalanine-containing fragments that serve as chiral elements in medicinal chemistry and biochemical research workflows.
3. Side-Chain Functionalization
Cbz-3-Methoxy-D-Phenylalanine is suitable for side-chain functionalization strategies that exploit the anisole-type 3-methoxy group while maintaining the amino acid framework for iterative synthesis. The aromatic methoxy substituent can be transformed into other functional motifs through oxidative demethylation, electrophilic aromatic substitution, or conversion to alternative oxygenated substituents that preserve the D-configuration at the α-carbon. The Cbz-protected amine supports orthogonal chemistry, allowing selective modification of the aromatic ring without premature loss of the α-amino protection. The resulting functionalized D-phenylalanine derivatives can feed into fragment elaboration, chiral intermediate preparation, and downstream synthesis of aromatic pharmacophores used in chemical biology and industrial fine chemical production.
4. Chemical Biology Labeling
Cbz-3-Methoxy-D-Phenylalanine is applied in chemical biology workflows that require stereodefined D-amino acid incorporation into probes, affinity tags, or enzyme-interaction studies. The protected α-amino group enables stepwise assembly into peptides or peptide-like conjugates, while the aromatic 3-methoxy group can serve as a stable substitution pattern during probe construction before later functional conversion. Controlled deprotection of the Cbz group can generate an amine for conjugation chemistry or for attachment of linkers used in biophysical assays and biomolecule modification. The D-phenylalanine stereochemistry helps provide defined backbone stereochemical features that can be important for studying recognition events, substrate specificity, or binding-site complementarity.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Methoxy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and process chemistry planning for chiral aromatic amino acid derivatives used in peptide-based or peptide-mimetic synthesis. The Cbz-protected amine provides a robust, isolable protection strategy that can be carried through coupling steps and then removed under conditions compatible with downstream transformations. The D-configuration at the α-carbon supports stereochemical control in manufacturing routes that require defined stereopurity for chiral building blocks. The aromatic 3-methoxy functionality offers a chemically meaningful substituent pattern for later conversion into other side-chain variants, enabling scalable synthesis of structured intermediates used in specialty chemical production and fine chemical manufacturing.
6. Analytical Standards in Peptide Chemistry
Cbz-3-Methoxy-D-Phenylalanine is used as an analytical reference material and method-development component in peptide chemistry where stereochemical and side-chain specificity must be tracked. The combination of Cbz protection and a 3-methoxy aromatic substituent yields a distinct chromatographic and mass spectrometric signature for monitoring protected amino acid consumption, peptide coupling progress, or impurity profiles. The D-stereocenter enables discrimination from L-configured analogs in chiral separation workflows and supports accurate assignment of stereochemistry in complex peptide mixtures. The compound's defined structure makes it suitable for calibrating analytical methods, supporting quality-by-design documentation in chemical manufacturing contexts, and enabling reliable tracking of aromatic side-chain modified peptide intermediates.
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