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Specifications
| Appearance | White or Off-white powder |
| Purity (HPLC) | 98% min |
| Specific Rotation [α]20/D | +25° ± 2° (C=1 in EtOH) |
| Melting Point | 140 ± 10 °C |
| Water Content (K.F) | 1.0% max |
| HNMR | In accordance with structure |
Applications
tert-Butyl L-tyrosinate (CAS 16874-12-7) is a protected amino acid derivative widely used in peptide synthesis and pharmaceutical research. The compound serves as a building block in solid-phase and solution-phase peptide synthesis, where the tert-butyl group protects the phenolic hydroxyl of L-tyrosine, preventing side reactions during peptide bond formation. It is employed in the development of bioactive peptides, enzyme inhibitors, and peptidomimetics, as well as in structure–activity relationship (SAR) studies to explore the effects of tyrosine residues on biological activity. Additionally, tert-Butyl L-tyrosinate is used as an intermediate in the synthesis of modified amino acids, peptide-based drugs, and chemical probes in medicinal chemistry.
Benefits
The benefits of tert-Butyl L-tyrosinate stem from its chemical stability, stereochemical integrity, and protective functionality. The tert-butyl group safeguards the phenolic hydroxyl during multi-step synthesis, allowing for selective reactions on the amino and carboxyl groups without unwanted side reactions. Its enantiomerically pure L-configuration ensures proper stereochemistry, which is crucial for biological activity and receptor recognition in peptides. The compound is also soluble in common organic solvents, facilitating incorporation into peptide chains and enabling high reaction efficiency. The ease of deprotection under mild acidic conditions further enhances its utility, allowing the recovery of free tyrosine for subsequent functionalization or final product formation.
Conclusion
tert-Butyl L-tyrosinate is a key protected amino acid intermediate with broad applications in peptide synthesis, drug discovery, and medicinal chemistry. Its combination of stereochemical purity, chemical stability, and protective functionality ensures efficient and selective synthesis of bioactive peptides and derivatives. By enabling precise molecular design and high-yield transformations, it remains an indispensable tool in modern peptide and pharmaceutical research.
