Thr-Phe links a polar threonine to an aromatic phenylalanine, forming a dipeptide that models hydrogen bonding and π-interactions. The sequence aids exploration of helix nucleation and β-turn formation. Researchers assess its conformational ensemble and solvent dependence. Applications include peptide-folding studies, enzyme-substrate modeling, and design of minimal recognition motifs.
CAT No: R2574
CAS No:16875-27-7
Synonyms/Alias:H-Thr-Phe-OH;Thr-Phe;16875-27-7;threonylphenylalanine;L-THREONYL-L-PHENYLALANINE;CHEBI:74862;TF dipeptide;T-F Dipeptide;threonyl-phenylalanine;Threoninylphenylalanine;L-Threoninyl-L-Phenylalanine;CHEMBL3321993;Threonine Phenylalanine dipeptide;Threonine-Phenylalanine dipeptide;(S)-2-((2S,3R)-2-Amino-3-hydroxybutanamido)-3-phenylpropanoic acid;(2S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]-3-phenylpropanoic acid;N-Threonylphenylalanine;(2S)-2-(((2S,3R)-2-amino-3-hydroxybutanoyl)amino)-3-phenylpropanoic acid;(2S)-2-(((2S,3R)-2-amino-1,3-dihydroxybutylidene)amino)-3-phenylpropanoate;(2S)-2-{[(2S,3R)-2-amino-1,3-dihydroxybutylidene]amino}-3-phenylpropanoate;L-3-Phenyl-N-L-threonylalanine;N-L-Threonyl-L-phenylalanine;15: PN: EP2161028 PAGE: 10 Claimed Protein;;MFCD00038591;L-Thr-L-Phe;Threoninyl-Phenylalanine;N-Threoninylphenylalanine;H-Thr-Phe-OH, AldrichCPR;N-L-Threonyl-L-phenylalanine;SCHEMBL233445;N-L-Threoninyl-L-phenylalanine;(2S)-2-[(2S,3R)-2-AMINO-3-HYDROXYBUTANAMIDO]-3-PHENYLPROPANOIC ACID;DTXSID101346616;HY-P4626;BDBM50049727;FT108188;CS-0655422;Q27144972;
Thr-Phe, also known as Threonylphenylalanine, is a dipeptide composed of threonine and phenylalanine linked via a peptide bond. As a structurally simple yet functionally versatile molecule, it serves as a valuable building block in peptide research and synthesis. Its unique combination of a polar hydroxyl group from threonine and a hydrophobic aromatic ring from phenylalanine grants it distinctive physicochemical properties, such as moderate solubility and the potential to participate in both hydrogen bonding and hydrophobic interactions. These characteristics make Thr-Phe an attractive compound for researchers exploring peptide structure-activity relationships, protein engineering, and the development of novel biomaterials. Its easy incorporation into longer peptide chains further enhances its utility in the design of custom peptides for various experimental applications.
Peptide Synthesis and Library Construction: Thr-Phe is widely used in the synthesis of peptide libraries for high-throughput screening and combinatorial chemistry studies. By incorporating this dipeptide into peptide sequences, researchers can systematically investigate how the presence of threonine and phenylalanine residues influences biological activity, receptor binding, or enzymatic recognition. Its versatility enables the generation of diverse peptide libraries, facilitating the discovery of new ligands, inhibitors, or bioactive compounds. The ability to introduce Thr-Phe at specific positions within a peptide chain also aids in the fine-tuning of peptide conformation and function, thereby supporting the rational design of peptides with tailored properties.
Protein Structure and Folding Studies: In the field of protein engineering and structural biology, Threonylphenylalanine serves as a useful probe for examining the effects of specific amino acid sequences on protein folding, stability, and tertiary structure. By substituting or inserting the dipeptide into model proteins or synthetic polypeptides, scientists can assess how the interplay between polar and hydrophobic side chains affects the overall folding landscape. Such studies provide valuable insights into the determinants of protein stability and the mechanisms underlying misfolding or aggregation, which are central to understanding many biological processes and pathologies.
Biomaterial Development: The unique side chain chemistry of Thr-Phe makes it a promising component in the design of peptide-based biomaterials and hydrogels. Its ability to engage in both hydrogen bonding and hydrophobic interactions can be harnessed to modulate the self-assembly behavior, mechanical properties, and biocompatibility of peptide-derived materials. Researchers utilize this dipeptide in the fabrication of scaffolds for tissue engineering, drug delivery systems, and cell culture substrates, where precise control over material properties is essential for optimizing biological performance.
Enzyme Substrate Specificity Research: Thr-Phe is often employed as a model substrate in enzymology studies, particularly for investigating the substrate specificity and catalytic mechanisms of proteases and peptidases. By utilizing this dipeptide in in vitro assays, researchers can elucidate the recognition motifs preferred by specific enzymes, map cleavage sites, and characterize enzyme kinetics. These findings contribute to a deeper understanding of enzyme function and inform the design of selective inhibitors or activity-based probes for biochemical and pharmacological research.
Analytical Method Development: The distinct chemical features of Thr-Phe make it an excellent standard or reference compound in the development and validation of analytical techniques, such as high-performance liquid chromatography (HPLC) and mass spectrometry (MS). Its defined structure and predictable retention behavior allow for the calibration of chromatographic systems and the optimization of detection parameters. As a result, it supports accurate quantification and identification of peptides in complex biological samples, enhancing the reliability of analytical workflows in proteomics and peptide chemistry.
In summary, Thr-Phe's multifaceted properties and functional versatility underpin its broad application across peptide synthesis, protein structure analysis, biomaterial innovation, enzyme specificity research, and analytical method development. Its strategic integration into experimental protocols enables scientists to probe fundamental questions in biochemistry, materials science, and analytical chemistry, driving forward advancements in peptide-based research and technology.
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