Fmoc-β-Ala-Pro-OH incorporates flexible β-alanine and conformationally restrictive proline in a protected form for synthetic use. The combination helps model turn formation and backbone curvature. Researchers evaluate its behavior in resin-bound assembly. Uses include structural motif construction, method optimization, and peptide scaffold development.
CAT No: R2524
CAS No:2171246-67-4
Synonyms/Alias:2171246-67-4;Fmoc-beta-Ala-Pro-OH;(S)-1-(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid;(2S)-1-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic acid;EN300-1502445;(S)-1-(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanoyl)pyrrolidine-2-carboxylicacid;(2S)-1-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoyl]pyrrolidine-2-carboxylic acid;(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanoyl)-L-proline; (2S)?-?1-?[3-?({[(9H-?fluoren-?9-?yl)?methoxy]?carbonyl}?amino)?propanoyl]?pyrrolidine-?2-?carboxylic Acid;
Fmoc-beta-Ala-Pro-OH is a synthetic dipeptide derivative featuring an N-terminal fluorenylmethyloxycarbonyl (Fmoc) protecting group, composed of beta-alanine and proline residues. As a building block in solid-phase peptide synthesis (SPPS), it plays a pivotal role in the generation of custom peptides, particularly those incorporating non-standard amino acid sequences or beta-amino acid motifs. The inclusion of both beta-alanine, an atypical amino acid, and proline, a cyclic imino acid, imparts unique conformational properties to peptides, making this compound especially relevant for researchers exploring peptide backbone modifications, structure-activity relationships, and novel biomimetic frameworks.
Peptide Synthesis: Fmoc-beta-Ala-Pro-OH is widely utilized as a protected dipeptide fragment in SPPS, enabling the efficient assembly of peptides containing beta-amino acid residues. Its Fmoc group provides orthogonal protection, allowing for selective deprotection and coupling steps under mild conditions. The presence of beta-alanine in the sequence expands the chemical diversity accessible to peptide chemists, facilitating the design of peptidomimetics and hybrid peptides with enhanced stability or altered biological profiles. By incorporating this dipeptide into synthetic protocols, researchers can introduce backbone modifications that modulate secondary structure or resistance to enzymatic degradation.
Conformational Studies: The combination of beta-alanine and proline within this dipeptide offers a valuable tool for investigating peptide folding and conformational dynamics. Beta-alanine introduces flexibility due to its extended backbone, while proline imposes conformational constraints through its cyclic structure. Incorporation of Fmoc-beta-Ala-Pro-OH into model peptides allows structural biochemists to probe the effects of beta-amino acid residues on turn formation, helix propensity, and overall peptide topology. Such studies contribute to the understanding of peptide structure-function relationships and inform the rational design of novel peptide-based materials.
Peptidomimetic Design: As a structurally distinctive motif, this dipeptide is instrumental in the development of peptidomimetics—synthetic molecules that mimic the functional properties of natural peptides. The inclusion of beta-alanine can enhance proteolytic stability and modify receptor interactions, while proline often serves as a key element in bioactive conformations. Researchers leverage Fmoc-beta-Ala-Pro-OH to create analogues with improved pharmacokinetic or physicochemical properties for use in biochemical assays, high-throughput screening, or as molecular probes in target validation studies.
Combinatorial Library Construction: The protected dipeptide is also employed in the generation of combinatorial peptide libraries, enabling the systematic exploration of sequence space for bioactive compounds. Its compatibility with automated SPPS platforms and orthogonal protection schemes allows for rapid incorporation into diverse peptide arrays. By using Fmoc-beta-Ala-Pro-OH as a building block, scientists can investigate the impact of beta-amino acid incorporation on binding affinity, selectivity, and functional activity across a wide range of biological targets.
Analytical Method Development: In addition to its synthetic applications, this dipeptide serves as a useful standard or reference compound in analytical method development for peptide characterization. Its unique sequence and physicochemical properties make it suitable for optimizing chromatographic separation, mass spectrometric detection, and structural elucidation protocols. Analytical chemists rely on such well-defined dipeptide derivatives to validate instrumentation, benchmark new methodologies, and ensure the accuracy of peptide analysis workflows.
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