Fmoc-β-Ala-Glu(OtBu)-OH combines a protecting group with a partially protected glutamate to facilitate solid-phase peptide synthesis. β-Alanine introduces flexibility within assembled sequences. Researchers use the building block to optimize coupling efficiency and structural progression. Applications include chain-elongation studies, synthetic development, and modular peptide design.
CAT No: R2521
CAS No:2411592-43-1
Synonyms/Alias:Fmoc-beta-Ala-Glu(OtBu)-OH;2411592-43-1;Fmoc--Ala-Glu(OtBu)-OH;(S)-2-(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanamido)-5-(tert-butoxy)-5-oxopentanoic acid;Fmoc-|A-Ala-Glu(OtBu)-OH;Fmoc-?-Ala-Glu(OtBu)-OH;MFCD31716167;CS-0439392;G74859;
Fmoc-beta-Ala-Glu(OtBu)-OH is a synthetic peptide building block featuring an Fmoc-protected beta-alanine linked to glutamic acid with tert-butyl protection on the side-chain carboxyl group. This compound is specifically designed for use in solid-phase peptide synthesis (SPPS), where its orthogonal protecting groups facilitate the stepwise assembly of complex peptide sequences. The unique combination of beta-amino acid and side-chain-protected glutamic acid allows researchers to introduce structural diversity and functional specificity into synthetic peptides, making it valuable for a variety of advanced biochemical investigations.
Peptide Synthesis: In the context of SPPS, Fmoc-beta-Ala-Glu(OtBu)-OH serves as a versatile monomer for constructing peptides that incorporate both beta-amino acid residues and protected glutamic acid side chains. The Fmoc group enables efficient N-terminal protection and deprotection cycles, while the tert-butyl ester ensures that the gamma-carboxyl group of glutamic acid remains inert during chain elongation. This orthogonal protection strategy allows for the precise incorporation of the building block at designated positions, supporting the synthesis of peptides with tailored backbone conformations and side-chain functionalities.
Peptidomimetic Design: The inclusion of a beta-alanine residue within the structure introduces conformational flexibility and resistance to enzymatic degradation, characteristics often exploited in the design of peptidomimetics. Researchers utilize Fmoc-beta-Ala-Glu(OtBu)-OH to generate analogs of bioactive peptides with enhanced metabolic stability or altered biological activity. Its use is particularly relevant in the development of novel peptide-based scaffolds for structure-activity relationship (SAR) studies and the exploration of noncanonical amino acid incorporation.
Structure-Function Studies: The presence of both a beta-amino acid and a protected glutamic acid residue makes this compound highly suitable for probing the effects of backbone modifications and side-chain functionalities on peptide structure and function. By integrating it into synthetic sequences, scientists can systematically investigate the impact of beta-amino acid substitution on peptide folding, receptor binding, or enzymatic recognition. Such studies contribute to a deeper understanding of peptide biophysics and inform the rational design of functionalized peptides.
Combinatorial Library Construction: Fmoc-beta-Ala-Glu(OtBu)-OH is frequently employed in the generation of combinatorial peptide libraries aimed at discovering novel ligands, inhibitors, or molecular probes. Its compatibility with automated peptide synthesizers and standard Fmoc/tBu protocols facilitates high-throughput synthesis of diverse peptide sequences. The ability to introduce both backbone and side-chain diversity expands the chemical space accessible to library designers, enabling more comprehensive screening of sequence-activity relationships.
Method Development and Optimization: The compound is also valuable in the optimization of synthetic protocols for challenging peptide sequences. Its defined protecting group scheme allows peptide chemists to troubleshoot and refine coupling, deprotection, and cleavage conditions, particularly when working with sequences prone to aggregation or side reactions. By serving as a model substrate or a component in test syntheses, it aids in the development of robust methodologies for the assembly of complex or non-standard peptides.
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