Boc-O-benzyl-L-tyrosine is a protected amino acid derivative in which the amino group is masked as a Boc carbamate and the carboxyl group is present as an O-benzyl ester, while the side chain retains the phenolic functionality characteristic of tyrosine. The molecule contains a chiral center consistent with the L-tyrosine framework and bears a benzyl-protected phenol (O-benzyl) that reduces phenolic acidity and modulates chemoselectivity during peptide coupling steps. In peptide synthesis workflows, this protected analogue functions as a stepwise building block that supports controlled reactivity of the amino and carboxyl functionalities and provides a stable handle for downstream deprotection and incorporation into peptide intermediates.
CAT No: CP02112
CAS No:2130-96-3
Synonyms/Alias:Boc-Tyr(Bzl)-OH;2130-96-3;Boc-O-benzyl-L-tyrosine;(S)-3-(4-(Benzyloxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid;N-Boc-O-benzyl-L-tyrosine;N-t-Boc-O-benzyl-L-tyrosine;N-(tert-Butoxycarbonyl)-O-benzyl-L-tyrosine;ST50331302;(2S)-3-[4-(benzyloxy)phenyl]-2-[(tert-butoxycarbonyl)amino]propanoicacid;54784-43-9;Boc-O-Bzl-L-Tyr;BOC-Tyr(Bzl);n-boc-o-benzyltyrosine;PubChem12949;AC1Q5XNP;N-Boc-O-Benzyl-tyrosine;N-Boc-(O-benzyl)tyrosine;N-tert-Butoxycarbonyl-O-benzyl-L-tyrisine;AC1L40EM;Boc-(O-benzyl)-L-tyrosine;15410_ALDRICH;SCHEMBL193473;15410_FLUKA;CTK1A1972;MolPort-003-926-780
Boc-O-benzyl-L-tyrosine is a protected L-tyrosine derivative designed for peptide and peptidomimetic synthesis, featuring a Boc-protected amino group and an O-benzyl-protected phenolic side chain. The tyrosine aromatic ring remains available for downstream deprotection and functionalization after peptide assembly, making this building block a practical choice for constructing peptides that require controlled phenol chemistry. In typical workflows, the orthogonal protection pattern supports reliable coupling while preserving side-chain integrity during fragment condensation and purification.
1. Solid-Phase Peptide Synthesis
Boc-O-benzyl-L-tyrosine is used by peptide synthesis groups to incorporate a tyrosine residue into protected peptide sequences where the phenolic oxygen must remain masked during chain assembly. The O-benzyl protection helps prevent undesired side reactions involving the tyrosine hydroxyl under coupling and deprotection conditions used in stepwise peptide construction, while the Boc amino protection supports controlled segment condensation strategies. Researchers developing peptide libraries and sequence-specific analogs often select this building block when they anticipate later phenol unmasking for subsequent derivatization or for generating native-like tyrosine after final deprotection.
2. Modified Tyrosine Peptides
Boc-O-benzyl-L-tyrosine is a common choice for preparing peptides intended for post-synthetic tyrosine chemistry, including workflows where the phenolic group is introduced or further functionalized after the peptide backbone is assembled. In chemical biology and protein engineering research, tyrosine residues are frequently leveraged as handles for site-specific modifications, and the O-benzyl protection enables the peptide to be carried through purification and handling steps without premature phenol reactivity. By using this protected tyrosine building block, developers can plan for downstream conversion of the tyrosine side chain into derivatives appropriate for binding studies, labeling strategies, or structure-activity relationship (SAR) analog sets.
3. Pharmaceutical Intermediate Development
Boc-O-benzyl-L-tyrosine is also employed in medicinal chemistry and pharmaceutical intermediate development as a protected tyrosine synthon for constructing tyrosine-containing fragments and intermediates. Teams preparing advanced intermediates for peptidomimetic scaffolds or tyrosine-functionalized leads often rely on the Boc/O-benzyl protection pattern to manage chemoselectivity across multi-step sequences. This reagent supports manufacturing-style workflows where protecting groups are chosen to withstand coupling and intermediate isolation, while enabling later deprotection steps to reveal the tyrosine functionality required for final assembly or conversion into the intended downstream chemical entity.
4. Peptide Segment Condensation
Boc-O-benzyl-L-tyrosine is used in solution-phase segment condensation and custom peptide manufacturing research when a protected tyrosine residue is required as part of a larger fragment strategy. The protected phenolic oxygen and Boc-protected amino group help maintain side-chain integrity during fragment coupling, allowing chemists to assemble longer sequences from pre-formed segments while minimizing side reactions that can complicate purification. This application is particularly relevant for laboratories building complex tyrosine-containing peptides where controlled deprotection timing is important for preserving sequence quality and enabling planned downstream tyrosine reactivity.
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