N-Fmoc-N-[4-(tert-butoxy)-4-oxobutyl]glycine is a protected glycine derivative bearing a bulky tert-butoxy group that influences coupling behavior. The extended side chain enables exploration of steric effects and linker design. Researchers use it in constructing complex peptidomimetics and modular scaffolds. Its structure supports orthogonal synthetic strategies.
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CAT No: R2128
CAS No:174799-90-7
Synonyms/Alias:174799-90-7;N-Fmoc-N-[4-(tert-butoxy)-4-oxobutyl]glycine;N-Fmoc-N-(4-(tert-butoxy)-4-oxobutyl)glycine;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-(4-(tert-butoxy)-4-oxobutyl)glycine;{[4-(tert-butoxy)-4-oxobutyl][(9H-fluoren-9-ylmethoxy)carbonyl]amino}acetic acid;Fmoc-{tBuOCO(CH2)3}Gly-OH;MFCD32898814;CS-0439257;2-[9H-fluoren-9-ylmethoxycarbonyl-[4-[(2-methylpropan-2-yl)oxy]-4-oxobutyl]amino]acetic acid;
N-Fmoc-N-[4-(tert-butoxy)-4-oxobutyl]glycine is a specialized amino acid derivative that features both an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group and a side chain modified with a tert-butoxy-substituted butanoyl moiety. As a reagent of significant interest in synthetic organic chemistry and peptide science, its unique structure enables selective incorporation into peptide chains or other biomolecules, providing a versatile handle for downstream modifications. The compound's dual protection and functionalization capacity make it valuable for researchers seeking to introduce non-standard side chains, expand chemical diversity, or engineer novel functionalities into peptides and related molecules.
Peptide synthesis: In solid-phase peptide synthesis (SPPS), derivatives like N-Fmoc-N-[4-(tert-butoxy)-4-oxobutyl]glycine serve as building blocks for the incorporation of modified glycine residues. The Fmoc group ensures compatibility with standard Fmoc/tBu-based protection strategies, allowing for efficient stepwise elongation of peptide chains. Its side chain modification offers researchers the ability to introduce steric bulk or chemical reactivity at specific positions within a peptide, facilitating the design of peptides with tailored structural or functional properties.
Peptide engineering: The compound's tert-butoxy- and oxobutyl-functionalized side chain provides a unique chemical motif that can be exploited in the development of peptidomimetics or backbone-modified peptides. By incorporating this derivative, scientists can modulate peptide backbone flexibility, enhance resistance to proteolytic degradation, or explore the effects of non-canonical side chains on biological activity and molecular recognition. Such modifications are particularly valuable in studies aiming to map structure-activity relationships or to design peptides with improved biophysical characteristics.
Chemical ligation strategies: N-Fmoc-N-[4-(tert-butoxy)-4-oxobutyl]glycine is also relevant in the context of advanced peptide ligation and conjugation methods. Its orthogonally protected functional groups allow for selective deprotection and subsequent chemical transformations, such as side chain elaboration or conjugation to other biomolecules. This versatility supports the assembly of complex peptide architectures, multifunctional probes, or bioconjugates for biochemical assays and molecular tool development.
Analytical method development: The modified glycine derivative can be used as a model substrate or reference standard in analytical chemistry, particularly in the optimization of chromatographic and spectrometric techniques for detecting and quantifying non-standard amino acid residues. Its unique mass and chromatographic properties aid in method validation, system suitability testing, and the calibration of analytical platforms used in peptide research and quality control.
Structure-activity relationship studies: Incorporation of this compound into peptide sequences enables systematic exploration of how specific side chain modifications influence biological function, molecular recognition, or physicochemical behavior. By introducing the tert-butoxy-4-oxobutyl group at defined positions, researchers can dissect the contributions of steric, electronic, and hydrophobic effects to peptide-receptor interactions, stability, or membrane permeability, thereby generating valuable insights for rational peptide design and optimization.
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