Fmoc-Ala-Phe-OH joins an aromatic residue with an aliphatic amino acid under a protective Fmoc group suited for solid-phase synthesis. The building block supports exploration of hydrophobic packing and structural initiation. Researchers assess coupling efficiency and folding contributions. Uses include peptide engineering, synthetic route development, and motif construction.
CAT No: R2522
CAS No:2171282-19-0
Synonyms/Alias:2171282-19-0;Fmoc--Ala-Phe-OH;EN300-1493172;(3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanoyl)-L-phenylalanine;(2S)-2-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanamido]-3-phenylpropanoic acid;
Fmoc--Ala-Phe-OH is a synthetic dipeptide protected at the N-terminus with a 9-fluorenylmethyloxycarbonyl (Fmoc) group, widely utilized in peptide chemistry and biochemical research. As a building block comprising alanine and phenylalanine residues, it plays a pivotal role in solid-phase peptide synthesis (SPPS), enabling the efficient assembly of custom peptide sequences. The Fmoc protection strategy offers orthogonality and compatibility with a variety of synthetic protocols, making this dipeptide an essential reagent for laboratories engaged in peptide engineering, structure-activity studies, and the development of functionalized biomolecules.
Peptide Synthesis: In the context of solid-phase peptide synthesis, Fmoc--Ala-Phe-OH serves as a pre-assembled dipeptide unit, streamlining the elongation of peptide chains. Its use reduces the number of coupling cycles required when incorporating both alanine and phenylalanine consecutively, enhancing synthetic efficiency and minimizing racemization risks. This approach supports the rapid generation of complex peptide libraries and facilitates the assembly of sequences with challenging motifs, ultimately advancing the field of custom peptide design.
Combinatorial Library Construction: The dipeptide is highly valuable in the construction of combinatorial peptide libraries for high-throughput screening applications. By providing a defined Ala-Phe motif, it enables systematic exploration of sequence diversity and aids in the identification of functional epitopes or bioactive peptide candidates. Its compatibility with automated synthesizers and standard Fmoc-based protocols ensures reliable incorporation into large-scale library formats, supporting drug discovery, enzyme substrate mapping, and receptor interaction studies.
Structure-Activity Relationship Studies: Researchers frequently employ Fmoc--Ala-Phe-OH in the synthesis of analogs for structure-activity relationship (SAR) investigations. The precise introduction of the Ala-Phe dipeptide segment allows for targeted modifications within peptide backbones, enabling the elucidation of key residues responsible for biological activity, binding affinity, or conformational stability. Such studies are instrumental in optimizing lead compounds and understanding the molecular determinants of peptide function.
Peptide Material Science: The protected dipeptide finds application in the development of peptide-based materials, such as hydrogels, nanostructures, or self-assembling systems. The hydrophobic and aromatic characteristics of the Ala-Phe sequence contribute to intermolecular interactions, influencing the assembly behavior and mechanical properties of peptide-derived materials. Its use in material science research facilitates the design of novel biomaterials for sensing, catalysis, or tissue engineering applications.
Analytical Method Development: Fmoc--Ala-Phe-OH is also employed as a reference compound or calibration standard in analytical method development, particularly in high-performance liquid chromatography (HPLC) and mass spectrometry. Its well-defined structure and predictable chromatographic behavior make it suitable for method validation, retention time calibration, and the assessment of peptide purity or identity during synthetic workflows. This utility supports quality assurance and process optimization in peptide production environments.
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