This glycine analog includes an extended aromatic ethyl substituent protected with Fmoc, offering steric tuning for peptide engineering. Researchers use it to explore linker rigidity, hydrophobic packing, and side-chain orientation. Its structural features allow controlled insertion into synthetic frameworks.
CAT No: R2104
CAS No:1286711-20-3
Synonyms/Alias:N-Fmoc-N-(2-(4-methoxyphenyl)ethyl)-Glycine;1286711-20-3;2-({[(9H-fluoren-9-yl)methoxy]carbonyl}[2-(4-methoxyphenyl)ethyl]amino)acetic acid;CS-0439215;G81922;
N-Fmoc-N-(2-(4-methoxyphenyl)ethyl)-Glycine is a synthetic derivative of glycine featuring an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group and a 2-(4-methoxyphenyl)ethyl substitution. As a specialized amino acid analog, it is primarily utilized in the context of solid-phase peptide synthesis (SPPS) and the development of structurally modified peptides. Its unique side chain modification introduces both steric and electronic properties, making it a valuable tool for researchers aiming to explore the structure-activity relationships (SAR) of peptide-based molecules. The Fmoc group offers orthogonal protection compatible with modern peptide assembly strategies, ensuring broad applicability in advanced peptide chemistry and related biochemical research.
Peptide Synthesis: Within the realm of synthetic peptide chemistry, this Fmoc-protected glycine analog is routinely incorporated as a building block during SPPS. Its compatibility with Fmoc-based deprotection protocols enables precise sequential addition to growing peptide chains, allowing for the introduction of non-standard amino acid residues. The 2-(4-methoxyphenyl)ethyl side chain not only expands the chemical diversity of synthetic peptides but also facilitates the design of analogs with altered hydrophobicity, aromatic character, or steric bulk. Researchers leverage these properties to systematically investigate the impact of side chain modifications on peptide folding, stability, and biological recognition.
Structure-Activity Relationship (SAR) Studies: The introduction of an aromatic and methoxy-substituted side chain at the glycine position provides a powerful means to probe the influence of specific residue modifications on the biological activity of peptides. By substituting canonical glycine with this analog, scientists can assess how changes in side chain electronics and bulk affect receptor binding, enzymatic processing, or protein-protein interaction profiles. Such SAR investigations are essential for the rational optimization of peptide-based ligands, inhibitors, or molecular probes in fundamental and applied research.
Peptide Backbone Conformation Analysis: The steric and electronic effects imparted by the modified side chain can induce conformational preferences in peptide backbones. This property is exploited in biophysical studies aimed at elucidating the relationship between side chain architecture and secondary structure formation. Incorporation of this glycine analog allows for the systematic modulation of local peptide geometry, aiding in the design of peptides with enhanced helical, turn, or extended conformations. Such studies contribute to the understanding of folding mechanisms and the engineering of peptides with tailored structural features.
Development of Peptidomimetics: The use of non-canonical amino acid derivatives like N-Fmoc-N-(2-(4-methoxyphenyl)ethyl)-Glycine is central to the creation of peptidomimetics—molecules that mimic the structure and function of natural peptides while offering improved stability or bioavailability. The aromatic and methoxy-functionalized side chain can confer resistance to proteolytic degradation or impart unique physicochemical properties, supporting the development of novel molecular scaffolds for research in chemical biology, drug discovery, or material science.
Analytical Method Development: Incorporation of this Fmoc-protected glycine analog into synthetic peptides can facilitate analytical studies such as high-performance liquid chromatography (HPLC) method optimization or mass spectrometric characterization. The distinctive chromophore and mass signature of the 2-(4-methoxyphenyl)ethyl group enable sensitive detection and reliable quantification of labeled peptides. Such attributes are particularly useful for validating synthetic protocols, monitoring reaction progress, or characterizing peptide libraries in research and development settings.
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