Fmoc-L-Phe-CHN2 contains an L-phenylalanine-derived amino acid framework in which the side chain is a benzyl group bearing a terminal diazo functionality (-CHN2), and the molecule is presented as an Fmoc-protected amino acid derivative for peptide-related synthesis. The structure includes a free carboxyl group and an Fmoc (9H-fluoren-9-ylmethoxycarbonyl) protecting group on the α-amino functionality, while the diazo group provides a distinct electrophilic/transferable functional handle for chemical labeling or crosslinking-style conjugation workflows. In synthetic and chemical biology contexts, this protected amino acid is employed as a building block in stepwise peptide assembly to introduce the diazo-bearing phenylalanine side chain for subsequent derivatization or analytical method development.
CAT No: CP25458
CAS No:172097-41-5
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-phenylalaninyl-diazomethane, (S)-3-Fmoc-amino-1-diazo-3-phenyl-2-butanone
Fmoc-L-Phe-CHN2 is an Fmoc-protected L-phenylalanine hydrazone derivative featuring a chiral amino acid core and a diazomethyl hydrazone-like functionality (CHN2) that can participate in nitrogen-rich intermediate chemistry. The structure combines an aromatic side chain typical of Phe-based peptide building blocks with an N-protected carbamate (Fmoc) that supports controlled amine deprotection during solid-phase or solution-phase peptide assembly. The terminal CHN2 functionality introduces a reactive nitrogen-containing handle that can be transformed or used as a synthetic equivalent in downstream derivatization, while the stereogenic center at the alpha carbon preserves the L-configuration associated with standard amino acid coupling behavior. The overall balance of aromatic hydrophobicity, protected amine stability, and a modifiable nitrogen functionality makes Fmoc-L-Phe-CHN2 suitable as a chiral intermediate for peptide chemistry and nitrogen-incorporating synthetic routes.
1. Peptide Synthesis
Fmoc-L-Phe-CHN2 is applied in peptide synthesis workflows where Fmoc protection enables orthogonal handling of the amino group and predictable coupling reactivity. The phenylalanine framework provides the canonical side-chain sterics and hydrophobic character used to construct peptide sequences and peptidomimetic scaffolds with defined aromatic spacing. The CHN2 functionality can be retained through peptide assembly steps and then leveraged for post-coupling transformation into nitrogen-containing motifs, allowing sequence-defined placement of a reactive handle. Downstream, the resulting peptide intermediates can support library generation, mechanistic studies of nitrogen incorporation, and synthetic access to labeled or functionalized peptide analogs. The compound thus functions as an amino acid building block that aligns with protected amino acid chemistry and controlled post-assembly derivatization.
2. Chemical Biology Probes
Fmoc-L-Phe-CHN2 is utilized in chemical biology research to introduce a nitrogen-rich functional handle into peptide-like structures for probe construction. The Fmoc-protected L-phenylalanine segment supports incorporation into defined peptide backbones, while the CHN2 group provides a reactive site that can undergo chemical conversion to generate probe-active derivatives. The aromatic side chain contributes to hydrophobic and π-interaction patterns that often influence binding or localization in target biomolecular contexts during probe design. The ability to position the CHN2 functionality at a specific residue level enables structure-function interrogation of peptide recognition elements and supports the synthesis of reactive intermediates for downstream conjugation strategies. Fmoc-L-Phe-CHN2 therefore serves as a chiral amino acid intermediate for designing peptide-based chemical probes with controlled functional placement.
3. Peptidomimetics And SAR
Fmoc-L-Phe-CHN2 is relevant to peptidomimetic and structure-activity relationship studies where nitrogen-containing modifications are used to tune physicochemical properties and interaction profiles. The L-phenylalanine core supplies a stereochemically defined backbone element that can be incorporated into analogs while maintaining the stereochemical fidelity typical of amino acid-derived scaffolds. The CHN2 functionality enables conversion into alternative nitrogen-bearing substituents, supporting systematic SAR exploration of how residue-level nitrogen chemistry affects binding conformations or stability. The Fmoc carbamate strategy supports stepwise synthesis of analogs that can be compared across series with consistent backbone geometry. The compound supports medicinal chemistry-oriented intermediate preparation for SAR studies involving amino acid derivatization and peptidomimetic construction.
4. Process Chemistry Intermediate
Fmoc-L-Phe-CHN2 can be employed as a process chemistry intermediate for manufacturing routes that require Fmoc-protected amino acid derivatives bearing a latent nitrogen functionality. The Fmoc group provides a robust protecting-group platform for handling, storage, and controlled deprotection under peptide-chemistry conditions, while the L-configuration supports stereochemically consistent downstream transformations. The CHN2 moiety can be designed into sequential synthetic steps that introduce nitrogen-containing functionality without disturbing the peptide-compatible protected amine during earlier stages. The aromatic phenylalanine side chain can be used to maintain hydrophobicity and reactivity patterns that align with standard amino acid coupling and intermediate purification strategies. Fmoc-L-Phe-CHN2 thus supports scalable fine chemical synthesis planning for nitrogen-incorporating amino acid derivatives and protected amino acid chemistry.
5. Analytical Standards And Labeling
Fmoc-L-Phe-CHN2 is suitable for analytical research and method development where defined amino acid-derived standards or derivatization precursors are required. The presence of a protected amino acid motif with an Fmoc group enables consistent incorporation into peptide-like structures used as reference materials for chromatographic or mass spectrometric workflows. The CHN2 functionality provides a handle for generating nitrogen-containing derivatives that can improve detectability or enable targeted derivatization strategies during analytical characterization. The stereochemically defined L-phenylalanine center supports the preparation of stereopure reference compounds for method validation involving chiral separation or stereochemical assignment. Fmoc-L-Phe-CHN2 therefore functions as a chiral amino acid intermediate for analytical standard development and residue-specific derivatization chemistry.
4. Cationic cell-penetrating peptides are potent furin inhibitors
5. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
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