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, also known as N-α-Fmoc-Alanyl-Phenylalanine, is a dipeptide derivative widely utilized in peptide synthesis and research. Featuring an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protective group, it enables efficient solid-phase peptide synthesis (SPPS) by ensuring selective deprotection and sequential elongation of peptide chains. The combination of alanine and phenylalanine imparts unique physicochemical properties, making this compound a valuable building block for constructing complex peptide sequences. Its chemical stability and compatibility with a variety of coupling reagents enhance its versatility in both academic and industrial laboratories focused on peptide engineering and functional analysis.
Peptide Synthesis: Fmoc-Ala-Phe-OH is primarily employed as a protected dipeptide in the assembly of larger peptides via SPPS. Researchers incorporate this compound into growing peptide chains to introduce the Ala-Phe motif with high fidelity and minimal racemization. The Fmoc group is easily removed under mild basic conditions, allowing for rapid and efficient chain elongation while preserving the integrity of side-chain functionalities. Its use streamlines the synthesis of peptides containing the Ala-Phe sequence, which is often found in bioactive peptides, enzyme substrates, and receptor ligands.
Peptide Structure-Activity Relationship (SAR) Studies: In medicinal chemistry and biochemical research, N-α-Fmoc-Alanyl-Phenylalanine serves as a critical component for probing the effects of sequence variations on peptide activity. By systematically incorporating this dipeptide into different positions within analogs, scientists can investigate how the Ala-Phe motif influences binding affinity, conformational stability, and overall biological function. Such SAR studies are essential for optimizing lead compounds in drug discovery and for understanding the molecular determinants of peptide-receptor interactions.
Combinatorial Peptide Library Construction: The protected dipeptide is frequently utilized in the generation of combinatorial peptide libraries for high-throughput screening applications. Its structural features facilitate the rapid synthesis of diverse peptide sequences, enabling the exploration of sequence space for novel bioactive compounds. By incorporating Fmoc-Ala-Phe-OH into library designs, researchers can efficiently generate and screen large numbers of variants to identify candidates with desirable properties such as improved binding, selectivity, or resistance to proteolysis.
Material Science and Biomaterials Development: Beyond traditional biochemical applications, Fmoc-Ala-Phe-OH finds utility in the development of peptide-based materials. Its incorporation into self-assembling peptide systems can modulate hydrophobicity, secondary structure formation, and intermolecular interactions. These features are exploited in the fabrication of nanostructures, hydrogels, and scaffolds for tissue engineering, drug delivery, and biosensing. The presence of the aromatic phenylalanine residue, in particular, can promote π-π stacking and other non-covalent interactions critical for material stability and function.
Enzyme Substrate Design: Researchers often use this dipeptide as a substrate or recognition element in enzymology studies. By integrating the Ala-Phe sequence into synthetic substrates, scientists can evaluate enzyme specificity, kinetics, and mechanism of action. This approach aids in elucidating the preferences of proteases and peptidases, as well as in the development of selective inhibitors or activity-based probes. The modular nature of Fmoc-Ala-Phe-OH allows for straightforward modification and adaptation to a variety of experimental setups, supporting detailed mechanistic investigations and the design of functional biomolecules.
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