N-Fmoc-N-(2-phenoxyethyl)glycine incorporates a flexible aromatic ether side chain that modifies polarity and conformational space. The residue is useful for linker design, hydrophobic tuning, and steric modulation in peptide engineering. Researchers employ it to examine solvent interactions and backbone alignment. Its Fmoc protection enables streamlined assembly.
CAT No: R2170
CAS No:2255321-25-4
Synonyms/Alias:2255321-25-4;SCHEMBL21837725;N-FMOC-N-(2-PHENOXYETHYL)GLYCINE;G81901;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-(2-phenoxyethyl)glycine;
N-Fmoc-N-(2-phenoxyethyl)glycine is a synthetic amino acid derivative featuring both a 9-fluorenylmethyloxycarbonyl (Fmoc) protective group and a 2-phenoxyethyl substituent on the glycine backbone. As a non-canonical amino acid, it is primarily utilized in the fields of peptide chemistry and chemical biology, where its unique side chain functionality and Fmoc protection offer valuable opportunities for controlled incorporation into synthetic peptides. The presence of the Fmoc group enables compatibility with standard Fmoc-based solid-phase peptide synthesis (SPPS) protocols, while the 2-phenoxyethyl modification can impart distinct physicochemical properties to resulting peptides, expanding the chemical diversity accessible to researchers. N-Fmoc-N-(2-phenoxyethyl)glycine serves as a versatile building block for the design of novel peptides and peptidomimetics, facilitating advanced studies in protein engineering, structure-activity relationship (SAR) analysis, and molecular recognition.
Peptide Synthesis: In the context of SPPS, incorporation of N-Fmoc-N-(2-phenoxyethyl)glycine allows chemists to introduce non-standard side chains into peptide sequences with high precision. The Fmoc protecting group ensures orthogonality with other protecting strategies, enabling stepwise assembly of complex peptides. Its compatibility with automated synthesizers and standard deprotection protocols streamlines the process, supporting the efficient generation of modified peptides for functional studies or as intermediates in the synthesis of more elaborate biomolecules.
Peptidomimetic Design: The 2-phenoxyethyl substituent on the glycine residue enables the creation of peptide analogs with enhanced conformational rigidity, altered hydrophobicity, or improved resistance to enzymatic degradation. By incorporating this derivative, researchers can systematically modify peptide backbones to probe the effects of side chain variation on biological activity, stability, or receptor binding. Such modifications are particularly valuable in the development of peptidomimetics for probing molecular interactions or as research tools in biochemistry and molecular pharmacology.
Structure-Activity Relationship Studies: Use of N-Fmoc-N-(2-phenoxyethyl)glycine in SAR investigations allows for the systematic exploration of how side chain modifications influence the function and binding properties of peptides. By substituting canonical glycine or other residues with this derivative, scientists can assess the impact of steric bulk, electronic properties, or aromatic interactions on target recognition, thereby gaining insight into critical determinants of peptide activity.
Bioconjugation and Probe Development: The unique chemical handle provided by the 2-phenoxyethyl group can be exploited for the design of bioconjugates or functional probes. Following peptide assembly and deprotection, the phenoxyethyl moiety may serve as a site for further chemical modification, such as the attachment of fluorescent labels, affinity tags, or other reporter groups. This enables the generation of custom molecular tools for applications in imaging, affinity purification, or mechanistic studies of protein-protein interactions.
Material Science and Supramolecular Chemistry: The incorporation of N-Fmoc-N-(2-phenoxyethyl)glycine into peptide-based materials or self-assembling systems can modulate the physicochemical properties and assembly behavior of the resulting constructs. The aromatic and ether functionalities of the side chain participate in non-covalent interactions, such as π-π stacking or hydrogen bonding, which can influence the formation of nanostructures, hydrogels, or other supramolecular architectures. Researchers in biomaterials and nanotechnology can leverage these attributes to tailor the assembly and function of peptide-derived materials for a range of experimental applications.
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