Fmoc-β-Ala-Ala-OH unites β-alanine flexibility with alanine's helix-forming tendencies under an Fmoc-protected framework. The building block supports synthesis of extended backbones and noncanonical linkers. Researchers examine coupling behavior and conformational influence during assembly. Applications include synthetic optimization, backbone engineering, and modular sequence design.
CAT No: R2520
CAS No:850324-83-3
Synonyms/Alias:Fmoc-beta-Ala-Ala-OH;850324-83-3;(S)-2-(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanamido)propanoic acid;Fmoc-|A-Ala-Ala-OH;MFCD30475812;BS-51363;E84053;EN300-1513555;(2S)-2-(3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanamido)propanoic acid;(2S)-2-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanamido]propanoic acid;(2S)-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoylamino]propanoic acid;
Fmoc-beta-Ala-Ala-OH is a synthetic dipeptide derivative featuring an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group, widely utilized in peptide chemistry and related biochemical research. As a building block comprising beta-alanine and alanine, this compound enables precise incorporation of non-standard amino acid motifs into peptide sequences, facilitating the exploration of peptide structure-function relationships and the development of novel bioactive molecules. Its unique configuration, combining a beta-amino acid with a standard alpha-amino acid, offers valuable opportunities for modulating peptide backbone flexibility, conformational stability, and resistance to enzymatic degradation, making it a versatile tool in advanced peptide synthesis and functional studies.
Peptide Synthesis: Fmoc-beta-Ala-Ala-OH is commonly employed as a protected dipeptide unit in solid-phase peptide synthesis (SPPS) protocols. The Fmoc group allows for orthogonal deprotection strategies, ensuring compatibility with established Fmoc/tBu chemistry. Incorporation of this dipeptide enables the introduction of beta-alanine residues into peptide chains, which can alter the overall conformational properties of the target peptide. Researchers leverage this compound to design and construct peptides with enhanced structural diversity, improved pharmacokinetic profiles, or specific backbone modifications that are otherwise challenging to achieve with standard amino acids alone.
Peptidomimetic Design: The inclusion of beta-amino acids, such as beta-alanine, within peptide sequences is a well-established strategy for generating peptidomimetics—molecules that mimic the biological activity of natural peptides but with improved stability and bioavailability. Fmoc-beta-Ala-Ala-OH serves as a key intermediate for synthesizing such analogues, enabling systematic investigation of the effects of backbone modifications on molecular recognition, receptor binding, and resistance to proteolytic enzymes. Its use supports the rational design of peptide-based probes, inhibitors, and ligands for fundamental research in chemical biology and drug discovery.
Structure-Activity Relationship Studies: Introducing a beta-alanine residue adjacent to alanine within a peptide backbone can significantly influence the spatial arrangement and flexibility of the resulting molecule. By incorporating this protected dipeptide into model peptides, scientists can probe the impact of beta-amino acid substitution on biological activity, receptor selectivity, and conformational dynamics. Such studies are essential for elucidating the structural determinants of peptide function and for optimizing lead compounds in early-stage research.
Biophysical Analysis: The presence of both beta- and alpha-amino acid residues in peptides synthesized using Fmoc-beta-Ala-Ala-OH offers a unique system for investigating secondary structure formation, folding kinetics, and aggregation behavior. Researchers utilize peptides containing this motif to study non-canonical helix and turn structures, as well as to explore the effects of backbone modifications on peptide-protein interactions. These investigations contribute valuable insights into the principles governing peptide self-assembly and stability.
Analytical Method Development: Fmoc-beta-Ala-Ala-OH can also be applied in the development and validation of analytical methods for peptide characterization. Its defined structure and unique chromatographic properties make it a useful reference standard or test substrate in high-performance liquid chromatography (HPLC), mass spectrometry, and capillary electrophoresis. By incorporating this compound into method development workflows, analytical scientists can optimize separation conditions, improve detection sensitivity, and ensure robust quantification of structurally diverse peptide species.
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