Fmoc-beta-Ala-Leu-OH unites flexible β-alanine with hydrophobic leucine for constructing extended backbones. The Fmoc group facilitates controlled coupling during solid-phase assembly. Researchers analyze the building block's contribution to conformation and packing. Applications include chain extension, synthetic-optimization studies, and modular peptide design.
CAT No: R2523
CAS No:848691-83-8
Synonyms/Alias:Fmoc-beta-Ala-Leu-OH;848691-83-8;Fmoc-|A-Ala-Leu-OH;G87282;EN300-1502597;(2S)-2-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanamido]-4-methylpentanoic acid;
Fmoc-beta-Ala-Leu-OH is a specialized dipeptide derivative featuring an Fmoc (9-fluorenylmethyloxycarbonyl) protecting group at the N-terminus, a beta-alanine residue, and a leucine residue at the C-terminus. Its unique structure, which incorporates both a non-proteinogenic beta-amino acid and a branched-chain hydrophobic amino acid, makes it a valuable building block in modern peptide synthesis. The Fmoc group enables orthogonal protection strategies, facilitating efficient solid-phase peptide synthesis (SPPS) and allowing for the selective deprotection and extension of peptide chains. As a result, this compound is highly regarded among researchers aiming to design custom peptides with enhanced properties, such as improved stability, bioactivity, or resistance to enzymatic degradation. Additionally, the incorporation of beta-alanine can impart increased conformational flexibility and influence the secondary structure of the resulting peptides, broadening the scope of potential applications in biochemical and biophysical studies.
Peptide Synthesis: Fmoc-beta-Ala-Leu-OH is widely used in the construction of linear and cyclic peptides via SPPS. Its compatibility with standard Fmoc chemistry protocols ensures seamless integration into automated or manual peptide assembly workflows. The beta-alanine residue acts as a spacer or structural modifier, allowing researchers to introduce flexibility or disrupt alpha-helical structures within peptide chains. This property is particularly valuable in the design of peptides intended for structure-activity relationship studies, where precise control over backbone conformation is essential for probing biological interactions and optimizing functional activity.
Peptidomimetic Design: The presence of beta-alanine in Fmoc-beta-Ala-Leu-OH provides an effective means to create peptidomimetics that mimic natural peptides while exhibiting enhanced metabolic stability. By substituting alpha-amino acids with beta-amino acids, researchers can generate analogs that resist proteolytic degradation and display altered binding profiles. Such peptidomimetics are instrumental in elucidating the roles of specific residues in protein-protein interactions, receptor recognition, and enzyme inhibition, thereby advancing the development of novel bioactive agents and research probes.
Combinatorial Chemistry: In the field of combinatorial library synthesis, Fmoc-beta-Ala-Leu-OH serves as a versatile scaffold for generating diverse peptide libraries. Its incorporation allows for the systematic exploration of sequence space, enabling the identification of lead compounds with desirable biological or physicochemical properties. The ability to introduce beta-alanine as a variable element expands the diversity and complexity of libraries, supporting high-throughput screening efforts in drug discovery, molecular recognition, and functional material development.
Structural Biology Studies: The dipeptide is frequently utilized in the synthesis of model peptides for structural investigations using techniques such as NMR spectroscopy and X-ray crystallography. Inclusion of beta-alanine and leucine residues can modulate peptide folding, aggregation, and self-assembly, providing insights into the determinants of secondary and tertiary structure. These studies contribute to a deeper understanding of peptide conformation, folding pathways, and the impact of non-canonical residues on structural dynamics.
Bioconjugation Research: Fmoc-beta-Ala-Leu-OH is employed in bioconjugation strategies where peptides are linked to various biomolecules, fluorophores, or surfaces for analytical and diagnostic applications. The dipeptide's sequence can be tailored to optimize linker length, flexibility, or hydrophobicity, thereby influencing the orientation and accessibility of conjugated moieties. This adaptability supports the development of multifunctional probes, biosensors, and affinity tags for use in proteomics, cell biology, and nanotechnology research.
Analytical Method Development: Researchers utilize Fmoc-beta-Ala-Leu-OH as a standard or reference compound in analytical method development for peptide characterization. Its defined structure and predictable chromatographic behavior make it suitable for validating separation techniques, optimizing detection parameters, and calibrating instrumentation. By serving as a benchmark in high-performance liquid chromatography (HPLC) or mass spectrometry workflows, the compound aids in ensuring the accuracy and reproducibility of peptide analysis, which is critical for quality control and method validation in both academic and industrial laboratories.
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