N-Fmoc-N-(2,2,2-trifluoroethyl)glycine incorporates a trifluoroethyl group that modifies polarity and electronic character. The residue is applied to examine fluorine-driven interactions and altered hydrogen-bonding patterns. Researchers employ it in designing peptides with unique conformational profiles. Its protected form aids controlled synthesis.
CAT No: R2135
CAS No:1486953-68-7
Synonyms/Alias:1486953-68-7;N-Fmoc-N-(2,2,2-trifluoroethyl)glycine;2-{[(9H-fluoren-9-ylmethoxy)carbonyl](2,2,2-trifluoroethyl)amino}acetic acid;2-[9H-fluoren-9-ylmethoxycarbonyl(2,2,2-trifluoroethyl)amino]acetic acid;2-({[(9h-fluoren-9-yl)methoxy]carbonyl}(2,2,2-trifluoroethyl)amino)acetic acid;{[(9H-fluoren-9-ylmethoxy)carbonyl](2,2,2-trifluoroethyl)amino}acetic acid;LJC95368;AKOS017496559;EN300-81360;F80622;N-(((9H-FLUOREN-9-YL)METHOXY)CARBONYL)-N-(2,2,2-TRIFLUOROETHYL)GLYCINE;
N-Fmoc-N-(2,2,2-trifluoroethyl)glycine is a synthetic amino acid derivative characterized by the presence of both a fluorenylmethyloxycarbonyl (Fmoc) protecting group and a trifluoroethyl-modified glycine backbone. As a non-canonical amino acid, it integrates the unique electronic and steric properties imparted by the trifluoroethyl substitution, alongside the standard Fmoc group commonly used for temporary N-terminal protection in solid-phase peptide synthesis. Its structural features make it a valuable tool for researchers seeking to introduce fluorinated functionalities into peptide chains or to explore the effects of such modifications on molecular recognition, stability, and bioactivity. The compound's relevance extends across peptide chemistry, medicinal chemistry, and the broader field of synthetic organic chemistry, where it enables precise control over molecular architecture and function.
Peptide Synthesis: N-Fmoc-N-(2,2,2-trifluoroethyl)glycine serves as a specialized building block in the assembly of custom peptides via solid-phase peptide synthesis (SPPS). The Fmoc group facilitates efficient stepwise elongation by providing orthogonal protection, while the trifluoroethyl modification introduces a distinct electronic environment and steric profile at the glycine position. This allows researchers to design peptides with enhanced metabolic stability, altered conformational preferences, or modified interaction profiles, which are critical parameters in the development of advanced biomolecular probes and functionalized peptide materials.
Structure-Activity Relationship Studies: Incorporation of this trifluoroethylated glycine analogue into peptide sequences enables detailed investigation of structure-activity relationships (SAR). The electron-withdrawing trifluoroethyl group can modulate local polarity, hydrogen bonding, and backbone rigidity, thereby influencing peptide folding, receptor binding, and biological activity. By systematically substituting standard glycine residues with this derivative, researchers can dissect the impact of fluorinated side chains on molecular recognition events and optimize lead compounds for improved performance in biochemical assays.
Fluorine-Labeling and Spectroscopic Probes: The presence of a trifluoroethyl group introduces three fluorine atoms, making peptides containing this residue amenable to ^19F NMR spectroscopy. This property is particularly valuable for tracking peptide conformation, dynamics, and interactions in complex biological or chemical environments, as fluorine atoms provide a sensitive and background-free spectroscopic handle. The compound thus supports the development of fluorinated probes for mechanistic studies, ligand screening, and the elucidation of protein-peptide interactions.
Development of Novel Peptidomimetics: The unique steric and electronic characteristics of N-Fmoc-N-(2,2,2-trifluoroethyl)glycine make it a strategic choice for the design of peptidomimetics—molecules that mimic the structure and function of natural peptides but with improved stability or altered activity. Incorporation of this derivative can enhance resistance to enzymatic degradation and introduce desirable pharmacokinetic properties, facilitating the exploration of new modalities in chemical biology and molecular recognition research.
Synthetic Organic Chemistry: Beyond peptide science, this Fmoc-protected, trifluoroethylated glycine derivative offers utility in broader synthetic applications where selective introduction of fluorine atoms is desired. Its use as a precursor or intermediate supports the generation of fluorinated small molecules, specialty polymers, or hybrid materials, enabling the study of fluorine's effects on chemical reactivity, material properties, and molecular interactions. The compound's compatibility with a range of coupling reagents and synthetic protocols further broadens its value for innovative research and development projects in modern organic synthesis.
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