Fmoc-2-Me-Nle-OH is a methylated norleucine derivative offering enhanced steric bulk and modulated hydrophobicity. Researchers use it to study helix formation, packing density, and side-chain interactions. Its modified structure supports design of stabilized peptidomimetic frameworks.
CAT No: R2169
CAS No:2226710-38-7
Synonyms/Alias:Fmoc-2-Me-Nle-OH;2226710-38-7;Fmoc-a-methyl-L-norleucine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylhexanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylhexanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-hexanoic acid;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-methylhexanoic acid;MFCD32263502;PB48168;CS-0312269;F81076;
Fmoc-2-Me-Nle-OH, also known as Fmoc-2-methyl norleucine, is a specialized amino acid derivative widely utilized in peptide synthesis and research. This compound features an Fmoc (9-fluorenylmethyloxycarbonyl) protecting group, which facilitates its integration into solid-phase peptide synthesis strategies. The presence of the methyl group at the 2-position of the norleucine backbone introduces unique steric and electronic properties, making it a valuable building block for the design of peptides with enhanced stability or altered biological activity. Its compatibility with standard peptide synthesis protocols and its ability to introduce noncanonical amino acid residues have positioned Fmoc-2-Me-Nle-OH as a versatile reagent in academic and industrial laboratories focused on peptide engineering and functional studies.
Peptide Synthesis: Fmoc-2-Me-Nle-OH is primarily employed in the assembly of custom peptides using solid-phase peptide synthesis techniques. By incorporating this non-natural amino acid into peptide chains, researchers can tailor the properties of their peptides, such as increasing hydrophobicity or introducing steric bulk. Its Fmoc protection allows for efficient coupling and deprotection cycles, ensuring high fidelity during chain elongation. This makes it particularly useful for synthesizing peptides that require precise control over sequence and structure, supporting both fundamental research and the development of novel biomolecules.
Structure-Activity Relationship Studies: In medicinal chemistry and biochemistry, 2-methyl norleucine derivatives are frequently used in structure-activity relationship (SAR) studies. The introduction of a methyl group can modulate the conformation of peptide backbones, enabling scientists to systematically investigate how side-chain modifications affect biological activity or receptor binding. By substituting canonical residues with Fmoc-2-Me-Nle-OH, researchers gain insights into the role of hydrophobic interactions, steric effects, and conformational constraints in peptide-receptor recognition or enzymatic processing.
Peptidomimetic Design: Fmoc-2-Me-Nle-OH serves as a valuable tool in the design of peptidomimetics—molecules that mimic the structure and function of peptides but with improved stability or bioavailability. The unique side-chain of 2-methyl norleucine can be used to disrupt proteolytic cleavage sites or to enhance the resistance of peptides to enzymatic degradation. This property is particularly advantageous when developing research tools or lead compounds intended for extended in vitro studies, as it allows for the creation of analogs with tailored stability profiles.
Protein Engineering: Incorporation of Fmoc-2-Me-Nle-OH into synthetic proteins or protein fragments is a strategy employed in protein engineering to probe the effects of side-chain modifications on folding, stability, and function. By replacing natural amino acids with this methylated analog, researchers can assess the influence of side-chain bulk and hydrophobicity on tertiary structure formation or intermolecular interactions. Such studies contribute to a deeper understanding of protein dynamics and inform the rational design of proteins with novel properties for research applications.
Biophysical and Analytical Applications: The altered physicochemical properties imparted by Fmoc-2-Me-Nle-OH make it suitable for biophysical and analytical studies. For example, peptides containing this residue are often used as calibration standards or reference compounds in chromatographic and mass spectrometric analyses. Its unique mass and retention characteristics help in the identification and quantification of peptides, as well as in the optimization of analytical protocols for complex peptide mixtures. These applications support the advancement of peptide science by enabling more accurate and reproducible experimental workflows.
In summary, Fmoc-2-Me-Nle-OH is an indispensable reagent for peptide synthesis, structure-activity relationship investigations, peptidomimetic design, protein engineering, and analytical method development. Its unique structural features and reliable performance in synthetic protocols make it a preferred choice for researchers aiming to expand the chemical and functional diversity of peptide-based molecules. Through its diverse applications, 2-methyl norleucine derivatives continue to drive innovation in peptide research and molecular design.
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