LSF(NO2)-Nle-AL-Methyl Ester Trifluoroacetate integrates nitroaromatic functionality with hydrophobic and polar residues, creating a versatile scaffold for interaction studies. The methyl ester supports controlled hydrolysis assays. Researchers evaluate conformational effects and solubility across conditions. Applications include ligand design, analytic chemistry, and sequence optimization.
CAT No: R2487
CAS No:99764-63-3
Synonyms/Alias:99764-63-3;LSF(NO2)-Nle-AL-Methyl Ester Trifluoroacetate;H-Leu-Ser-p-nitro-Phe-Nle-Ala-Leu-OMe trifluoroacetate salt;methyl (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-nitrophenyl)propanoyl]amino]hexanoyl]amino]propanoyl]amino]-4-methylpentanoate;2,2,2-trifluoroacetic acid;H-Leu-Ser-Phe(NO2)-Nle-Ala-OMe (TFA);H-LEU-SER-P-NITRO-PHE-NLE-ALA-LEU-OME TFA;(2S,5S,8S,11S,14S,17S)-Methyl 17-amino-8-butyl-14-(hydroxymethyl)-2-isobutyl-5,19-dimethyl-11-(4-nitrobenzyl)-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaicosan-1-oate 2,2,2-trifluoroacetate;MFCD00211055;HY-P3725;H-Leu-Ser-Phe(NO2)-Nle-Ala-OMe TFA;DA-54036;FL110873;CS-0619899;H-Leu-Ser-P-Nitro-Phe-Nle-Ala-Leu-OMe-Tfa;G85478;
LSF(NO2)-Nle-AL-Methyl Ester Trifluoroacetate is a specialized carbohydrate-based compound that integrates a nitro-functionalized sulfonyl fluoride group, norleucine, and an alanine methyl ester, stabilized as a trifluoroacetate salt. This unique molecular design offers remarkable stability and reactivity, making it an invaluable building block in synthetic chemistry and biochemical research. Its structural features facilitate selective modifications and conjugations, supporting advanced studies in glycoscience, peptide chemistry, and molecular labeling. The presence of the nitro group and sulfonyl fluoride moiety enhances its electrophilic character, broadening its utility in various chemical transformations and enabling researchers to develop novel methodologies for probing biological systems.
Peptide Synthesis: LSF(NO2)-Nle-AL-Methyl Ester Trifluoroacetate serves as a valuable intermediate in solid-phase and solution-phase peptide synthesis. Its incorporation allows for the introduction of non-canonical amino acids, such as norleucine, and site-specific modifications that can modulate peptide function and stability. The methyl ester functionality provides a convenient handle for subsequent deprotection or derivatization, supporting the generation of tailored peptide sequences for structure-activity relationship studies and functional assays. This compound's compatibility with standard coupling reagents and protocols ensures efficient integration into automated synthesis workflows, facilitating the rapid development of novel peptide-based probes and therapeutics.
Chemical Biology Probes: The nitro-functionalized sulfonyl fluoride group in this carbohydrate compound enables the design of covalent chemical probes for interrogating enzyme function and protein interactions. By reacting selectively with nucleophilic amino acid residues, such as serine, lysine, or cysteine, it can irreversibly label target proteins, allowing for activity-based protein profiling and target identification in complex biological samples. Researchers leverage this reactivity to map enzyme active sites, study post-translational modifications, and validate drug targets, advancing the understanding of cellular signaling pathways and protein networks.
Bioorthogonal Labeling: LSF(NO2)-Nle-AL-Methyl Ester Trifluoroacetate is well-suited for bioorthogonal labeling strategies, where its unique functional groups facilitate selective conjugation reactions under physiological conditions. The sulfonyl fluoride moiety participates in SuFEx (Sulfur(VI) Fluoride Exchange) chemistry, enabling the attachment of fluorescent dyes, affinity tags, or other reporter groups without interfering with native biomolecules. This approach supports the visualization and tracking of biomolecules in live-cell imaging, proteomics, and interactome analyses, providing powerful tools for studying dynamic biological processes with high specificity and minimal background labeling.
Medicinal Chemistry Research: In the realm of medicinal chemistry, this compound is explored for the design and synthesis of novel pharmacophores and peptidomimetics. Its structural versatility allows medicinal chemists to incorporate functionalized side chains and optimize molecular properties such as solubility, membrane permeability, and target binding affinity. By serving as a scaffold for the development of enzyme inhibitors, receptor ligands, or molecular glues, it contributes to the discovery of new chemical entities with potential therapeutic applications. The ability to fine-tune reactivity and selectivity through structural modifications further enhances its value in hit-to-lead optimization and mechanistic studies.
Glycoconjugate Synthesis: The trifluoroacetate salt form of LSF(NO2)-Nle-AL-Methyl Ester facilitates its use in the synthesis of glycoconjugates, which are essential for studying carbohydrate-mediated biological recognition events. It can be employed to link peptides or small molecules to carbohydrate moieties, generating hybrid structures that mimic natural glycoproteins or glycolipids. These conjugates are instrumental in investigating cell-surface interactions, immune recognition, and pathogen-host dynamics. By enabling the precise construction of structurally defined glycoconjugates, this compound supports the development of molecular probes, vaccine candidates, and diagnostic tools in glycoscience research.
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