Cbz-4-Cyano-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a 4-cyano substituent on the aromatic ring. The molecule contains an amino functionality masked as a benzyloxycarbonyl (Cbz) carbamate and a free carboxyl group, while the side chain presents a phenyl ring substituted with a nitrile that provides a polar, electronically defined handle for structure-activity and conformational studies. As a protected amino acid intermediate, it is used in peptide synthesis workflows to introduce the 4-cyano phenylalanine motif with controlled chemoselectivity and to support preparation of labeled or modified peptide analogues for chemical biology and analytical method development.
CAT No: CP11909
Cbz-4-Cyano-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyl carbamate (Cbz) on the amino group and a para-cyano substituent on the aromatic side chain. The molecule combines a protected α-amino functionality with a stereogenic center at the α-carbon, while the nitrile group provides a strongly polarized handle for subsequent transformations. The aromatic ring and nitrile-bearing side chain modulate polarity and can influence peptide conformation and binding-site interactions in structure-activity relationship studies. As a chiral, N-protected amino acid building block, it is suitable for stepwise peptide coupling chemistry and for downstream conversion into functionalized aromatic or heteroaromatic motifs.
1. Peptide Synthesis
Cbz-4-Cyano-D-Phenylalanine supports peptide building-block workflows in solid-phase or solution-phase synthesis where an N-Cbz-protected amino acid is required for controlled amide bond formation. The Cbz carbamate protects the α-amine during coupling, while the D-stereocenter enables incorporation of defined stereochemistry into peptide sequences and peptidomimetic scaffolds. The para-cyano group remains stable under many coupling conditions and can survive as a latent functional group for later derivatization after peptide assembly. The resulting nitrile-bearing peptide analogs can be used to probe backbone/side-chain recognition patterns and to generate defined intermediates for further functional group conversion.
2. Side-Chain Functionalization
Cbz-4-Cyano-D-Phenylalanine enables side-chain functionalization strategies that leverage the aromatic nitrile as a chemically addressable handle for synthetic organic chemistry. The nitrile can be converted to amide, carboxylic acid, amidine, or heterocycle precursors depending on the chosen transformation sequence, while the Cbz group provides a removable protection point for orthogonal functionalization timing. The D-phenylalanine stereochemistry helps maintain stereochemical fidelity when the nitrile is transformed into polar or ring-forming substituents in downstream derivatives. The compound therefore serves as a controlled chiral intermediate for generating nitrile-to-functional group libraries used in SAR studies and medicinal-chemistry style fragment elaboration.
3. Chiral Amino Acid Intermediate
Cbz-4-Cyano-D-Phenylalanine functions as a chiral amino acid intermediate for asymmetric synthetic routes that require a protected D-phenylalanine framework with an electronically tuned aromatic substituent. The combination of Cbz-protected amine and the para-cyano aromatic group allows staged deprotection and selective side-chain chemistry without losing the stereochemical information at the α-carbon. The nitrile-bearing phenyl ring can influence reactivity and solubility profiles during intermediate handling, which can be relevant when designing scalable fine-chemical synthesis sequences. The compound can be applied to the preparation of D-amino acid derivatives, peptide fragments, and chiral building blocks used to construct stereodefined molecular scaffolds.
4. Peptidomimetics And SAR
Cbz-4-Cyano-D-Phenylalanine is suitable for peptidomimetic construction where controlled incorporation of a D-amino acid residue and a nitrile-bearing aromatic side chain helps tune physicochemical and binding-relevant properties. The Cbz-protected α-amine supports sequential coupling to form amide-linked analogs, while the para-cyano substituent can act as a polar vector that participates in specific intermolecular interactions or serves as a precursor for further side-chain elaboration. The stereodefined D-configuration can be used to modulate peptide-like conformation and protease resistance in structure-activity relationship studies without changing the core coupling chemistry. Downstream conversion of the nitrile into alternative functional groups enables systematic analog generation for mapping structure-function relationships.
5. Pharmaceutical Intermediate Preparation
Cbz-4-Cyano-D-Phenylalanine can be employed in pharmaceutical intermediate preparation where protected amino acid derivatives are required for controlled assembly of complex nitrogen-containing intermediates. The Cbz group provides a stable protecting-group strategy during multi-step synthesis, and the α-amino protection facilitates predictable peptide coupling or amide formation when building higher-molecular-weight intermediates. The aromatic nitrile offers a robust functional handle for later conversion into amide or acid forms, enabling route design that connects chiral amino acid supply to downstream heteroatom-functional intermediates. The compound's defined stereochemistry and protected functionality make it applicable to manufacturing-oriented fine chemical synthesis of chiral building blocks used in iterative process development.
6. Analytical Research Standards
Cbz-4-Cyano-D-Phenylalanine is appropriate for analytical research and method development where chiral, N-protected amino acid standards are needed to monitor derivatization, coupling efficiency, or stereochemical integrity. The presence of the Cbz group and the para-cyano substituent provides distinct chromatographic and mass spectrometric signatures that can support identification of the protected amino acid and its conversion products. D-stereochemistry can be leveraged to discriminate enantiomeric mixtures during quality-focused studies of amino acid derivative workflows. The compound can therefore serve as a reference material for validating analytical strategies tied to protected amino acid synthesis, peptide building-block handling, and nitrile-to-functional group transformation tracking.
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