Fmoc-2-Me-Nval-OH is an Fmoc-protected methylated norvaline analog offering increased steric constraint. The modified side chain influences backbone orientation and helix propensity. Researchers use it to engineer hydrophobic cores and study conformational restriction. Its properties support fine control in peptide synthesis.
CAT No: R2127
CAS No:881921-10-4
Synonyms/Alias:Fmoc-2-Me-Nval-OH;881921-10-4;Fmoc-a-methyl-L-norvaline;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpentanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpentanoic acid;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-methylpentanoic acid;SCHEMBL19220445;DTXSID401195264;MFCD32263503;CS-0356169;G63174;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-methyl-L-norvaline;
Fmoc-2-Me-Nval-OH, also known as Fmoc-2-Methyl-norvaline, is a synthetic, Fmoc-protected, non-proteinogenic amino acid widely utilized in peptide chemistry and advanced biochemical research. Structurally, it features a methylated norvaline backbone, introducing unique steric and hydrophobic properties that are not present in standard amino acids. The Fmoc group serves as a temporary protecting group for the amino function, facilitating its incorporation into solid-phase peptide synthesis (SPPS) workflows. This compound is instrumental for researchers aiming to explore the effects of side-chain modifications on peptide structure, function, and stability, and it provides a versatile tool for the development of novel peptide-based biomolecules.
Peptide Synthesis: In the context of solid-phase peptide synthesis, Fmoc-2-Me-Nval-OH enables the site-specific introduction of a methylated norvaline residue into peptide sequences. The Fmoc protection ensures compatibility with standard Fmoc/tBu SPPS protocols, allowing for efficient coupling and deprotection cycles. By incorporating this non-canonical amino acid, researchers can systematically investigate how side-chain methylation influences peptide folding, aggregation propensity, and resistance to enzymatic degradation, supporting the design of peptides with enhanced biophysical or pharmacological properties for research applications.
Peptidomimetic Design: The methyl group on the norvaline side chain imparts increased steric bulk and hydrophobicity, making this derivative a valuable building block for peptidomimetic design. Inclusion of 2-Me-Nval within peptide analogs can modulate backbone conformation and side-chain interactions, which is critical for the development of bioactive molecules with improved receptor selectivity or altered biological activity. Such modifications are particularly relevant in the study of protein-protein interactions, enzyme inhibition, and molecular recognition processes where subtle changes in amino acid structure can have significant functional consequences.
Structure-Activity Relationship Studies: The unique properties of Fmoc-2-Me-Nval-OH make it a powerful tool for systematic structure-activity relationship (SAR) investigations. By substituting natural residues with 2-methyl-norvaline in model peptides, researchers can probe the impact of side-chain bulk and hydrophobicity on biological activity, binding affinity, and conformational stability. These insights are essential for rational peptide optimization, enabling the fine-tuning of sequence properties to achieve desired functional outcomes in biochemical assays and molecular interaction studies.
Protease Resistance Engineering: Incorporation of methylated norvaline residues into peptide backbones can enhance resistance to proteolytic degradation. The steric hindrance provided by the methyl group can impede recognition and cleavage by common proteases, extending the half-life of synthetic peptides in enzymatic environments. This application is particularly valuable in the development of peptide probes, molecular tools, and research reagents that require increased stability during in vitro or ex vivo studies, supporting more reliable experimental outcomes.
Analytical Method Development: Fmoc-2-Me-Nval-OH serves as a useful standard and reference compound in the development and validation of analytical methods for peptide characterization. Its distinct chemical structure and chromatographic behavior make it an ideal candidate for optimizing HPLC, mass spectrometry, and related analytical techniques. Utilizing this compound in method development enables accurate detection, quantification, and identification of methylated amino acid residues within complex peptide mixtures, contributing to robust quality control and research reproducibility in peptide science.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More