Boc-L-tyrosine is an N-Boc-protected L-tyrosine amino acid derivative, featuring the phenolic aromatic side chain characteristic of tyrosine alongside a free carboxylic acid group and an N-terminus masked by a tert-butoxycarbonyl (Boc) protecting group. The molecule contains both amino and carboxyl functionalities, with the amino group converted into a carbamate (Boc) to suppress undesired amine reactivity, while the tyrosine phenol remains available for chemoselective derivatization or hydrogen-bonding interactions. In peptide chemistry, Boc-L-tyrosine is employed as a stepwise building block for controlled incorporation of the tyrosine residue into peptides and peptide-related intermediates, where the protecting group supports selective transformations of side-chain and carboxyl functions during synthesis and purification.
CAT No: CP02108
CAS No:3978-80-1
Synonyms/Alias:Boc-Tyr-OH;Boc-L-tyrosine;3978-80-1;N-Boc-L-tyrosine;N-(tert-Butoxycarbonyl)-L-tyrosine;N-Boc-tyrosine;Boc-D-phe(4-OH)-OH;CHEMBL65386;CNBUSIJNWNXLQQ-NSHDSACASA-N;N-T-BUTOXYCARBONYL-L-TYROSINE;N-(TERT-BUTOXYCARBONYL)TYROSINE;ST092306;N-(TERT-BUTYLOXYCARBONYL)-L-TYROSINE;L-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-;(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionicacid;(2S)-2-[(tert-butoxy)carbonylamino]-3-(4-hydroxyphenyl)propanoicacid;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-HYDROXYPHENYL)PROPANOICACID;N-alpha-t-BOC-L-TYROSINE;Boc-tyrosine;Boc-(L)-tyrosine;N-t-BOC-L-Tyrosine;BOC-TYROSINE-OH;PubChem12233;(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;t-butyloxycarbonyltyrosine
Boc-L-tyrosine is an N-Boc protected L-tyrosine building block featuring a phenolic side chain that is commonly leveraged for constructing tyrosine-containing peptide segments. The Boc group on the amino terminus provides acid-labile protection that aligns with standard peptide assembly workflows, while the tyrosine side chain enables downstream functionalization or incorporation into peptides requiring aromatic residues. This protected amino acid is widely used by peptide synthesis groups and intermediate developers who need a controlled, bench-stable reagent for tyrosine positioning within protected peptide fragments.
1. Solid-Phase Peptide Synthesis
Boc-L-tyrosine is used as a protected tyrosine residue source for custom peptide synthesis workflows where N-terminal protection strategy is critical for stepwise chain assembly. Peptide chemistry teams typically incorporate this building block into tyrosine-containing sequences to ensure the amino functionality remains protected during coupling and deprotection cycles, while the phenolic side chain provides a defined aromatic handle for later peptide-level modification strategies. Because the reagent is pre-protected at the amino terminus, it fits into peptide manufacturing and research-grade synthesis pipelines that prioritize reproducible fragment construction and controlled deprotection behavior.
2. Tyrosine-Containing Segment Building
Boc-L-tyrosine supports the development of intermediate peptide segments and protected amino-acid fragments used in both solution-phase and hybrid peptide assembly approaches. Peptide developers rely on it to position the tyrosine residue at specific sites within longer constructs, enabling consistent handling of the aromatic side chain during segment condensation and purification. In practice, this reagent is selected when the synthesis plan requires a Boc-protected amino terminus for compatibility with the chosen coupling/deprotection schedule, while preserving the tyrosine side chain for subsequent transformations at the peptide or segment level.
3. Pharmaceutical Intermediate Development
Boc-L-tyrosine is frequently deployed in pharmaceutical intermediate programs that require tyrosine-derived protected building blocks for the preparation of peptide-like scaffolds, conjugation precursors, or tyrosine-functionalized intermediates. Process development and medicinal chemistry groups use the reagent to generate defined tyrosine-containing fragments with controlled protection of the amino group, supporting downstream derivatization steps that depend on the aromatic phenolic functionality. This positioning as a protected amino acid intermediate makes it a practical choice for teams building complex, tyrosine-bearing structures where reproducibility and protection-state control are essential for scale-up-friendly synthetic planning.
4. Aromatic Side-Chain Functionalization
Boc-L-tyrosine is used when the phenolic side chain must be carried through early stages of synthesis in a protected amino-acid form, then transformed later to introduce tyrosine-derived functionality. Chemical biology and peptide engineering groups often select this reagent to prepare tyrosine-bearing intermediates that can be further modified after peptide assembly or during fragment elaboration, leveraging the presence of the aromatic phenol as a reactive site. This workflow is particularly common when the synthesis strategy separates "backbone construction" from "side-chain tailoring," allowing the tyrosine residue to be introduced early and functionalized at a later, more controlled stage.
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