Cbz-3-Cyano-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing a nitrile substituent at the 3-position of the aromatic side chain, placing it in the class of nonstandard amino acid building blocks for peptide chemistry. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) protecting group that masks the amino functionality and a free carboxyl group, while the side chain features a cyano group that adds strong electron-withdrawing character and a chemically distinct handle for structure-activity and conformational studies. As a protected amino acid intermediate, it is used in peptide synthesis workflows to introduce the 3-cyano-phenylalanine motif with controlled chemoselectivity at the amine, supporting the preparation of peptides and peptide analogues for chemical biology and analytical method development.
CAT No: CP11809
Cbz-3-Cyano-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) carbamate on the amino group and a 3-cyano substituent on the aromatic ring, creating a chiral amino acid framework with an additional nitrile handle. The Cbz-protected amine supports amide bond formation under peptide coupling conditions while remaining stable to many base-mediated transformations, and the aromatic nitrile introduces a strongly electron-withdrawing functional group that can influence reactivity and downstream derivatization. The compound's stereochemistry at the α-carbon enables incorporation into peptide sequences or peptidomimetic scaffolds where D-amino acid stereochemical control affects conformational preferences and proteolytic stability. The nitrile can participate in chemoselective transformations such as reduction, cyclization, or conversion to other nitrogen-containing motifs, making the molecule a useful chiral intermediate for amino acid derivatization and synthetic diversification.
1. Peptide Synthesis
Cbz-3-Cyano-D-Phenylalanine is applied in peptide building workflows where a Cbz-protected D-amino acid component is required for controlled N-terminal protection and subsequent coupling. The protected carbamate and the α-carboxyl group allow standard peptide coupling strategies to generate amide linkages while preserving the aromatic nitrile substituent for later functional group manipulation. D-stereochemistry supports the construction of peptide analogs with altered backbone stereochemical patterns, which can be leveraged in structure-activity relationship studies and peptide stability assessments. The aromatic nitrile further enables downstream conversion into diversified side-chain functionalities without losing the amino acid backbone integrity.
2. Peptidomimetics And SAR
Cbz-3-Cyano-D-Phenylalanine is suited to peptidomimetic design and SAR-oriented scaffold generation where a D-phenylalanine motif bearing a nitrile-substituted aromatic ring is used to tune electronic and steric properties. The Cbz group provides a removable N-protection strategy for stepwise assembly of analog series, while the nitrile serves as a chemically addressable handle that can be transformed into amines, heterocycles, or other polar substituents to probe binding interactions. The chiral α-center supports stereochemically defined analog libraries, enabling systematic evaluation of how D-configuration and side-chain electronics affect molecular recognition. The resulting derivatives can be used as research-grade intermediates for medicinal chemistry campaigns focused on amino acid-derived pharmacophores.
3. Side-Chain Functionalization
Cbz-3-Cyano-D-Phenylalanine is used for side-chain functionalization routes that exploit the aromatic nitrile as a platform for additional nitrogen chemistry. The nitrile's electrophilic carbon can undergo selective reductions or cyclization strategies to generate new functional groups while the Cbz-protected amine helps maintain chemoselectivity during multi-step transformations. The D-amino acid scaffold allows the functionalized products to retain compatibility with peptide coupling or further amino acid derivatization, supporting the preparation of substituted aromatic side-chain analogs. Downstream conversion of the nitrile enables access to diverse functionalized building blocks for chemical biology probes and synthetic organic chemistry intermediate preparation.
4. Chiral Amino Acid Intermediate
Cbz-3-Cyano-D-Phenylalanine functions as a chiral amino acid intermediate for stereochemically controlled synthesis of protected amino acid derivatives and downstream peptide building blocks. The D-configuration at the α-carbon provides a defined stereochemical input for asymmetric structure construction, while the Cbz carbamate offers a practical protection strategy that can be removed when free amine chemistry is required. The aromatic nitrile contributes an additional functional group that can be preserved through protection and coupling steps or converted later to expand the chemical space of derivative compounds. The compound can therefore serve as a reliable intermediate in fine chemical synthesis and process chemistry workflows that require chiral, protected amino acid inputs with orthogonal functional group reactivity.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Cyano-D-Phenylalanine is relevant to pharmaceutical intermediate preparation where protected amino acid fragments are manufactured for incorporation into peptide-like or amino acid-derived structures. The Cbz-protected amine and carboxyl functionality enable controlled conversion into activated coupling partners or protected derivatives used in multi-step synthesis toward larger molecules. The aromatic nitrile provides a handle for late-stage diversification, supporting manufacturing routes that generate multiple analogs from a common chiral precursor without changing the stereochemical core. The compound's structural features align with industrial synthetic planning for chiral building blocks used in specialty chemical production and process development for amino acid-based intermediates.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More