Boc-D-tyrosine is a protected D-configuration amino acid derivative in which the tyrosine side chain (phenolic aromatic ring) is attached to a backbone bearing an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains both an amino functionality masked as a carbamate by Boc and a free carboxylic acid group, with the phenolic hydroxyl on the aromatic side chain providing a hydrogen-bonding and phenol-reactive handle while the stereochemistry is specified as D. As a stepwise peptide synthesis intermediate, the Boc-protected amino group supports controlled coupling chemistry while the free carboxyl group enables formation of peptide bonds and the tyrosine phenol can be used for subsequent derivatization or orthogonal functionalization during peptide and amino acid conjugate preparation.
CAT No: CP02107
CAS No:70642-86-3
Synonyms/Alias:Boc-D-tyrosine;70642-86-3;Boc-D-Tyr-OH;N-(tert-Butoxycarbonyl)-D-tyrosine;N-Boc-D-tyrosine;Boc-L-phe(4-OH)-OH;CHEMBL302367;N-ALPHA-T-BUTOXYCARBONYL-D-TYROSINE;(R)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionicacid;(2R)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicacid;AmbotzBAA1300;PubChem12014;N-alpha-t-Boc-D-tyrosine;KSC496E6J;15187_ALDRICH;AC1LU894;SCHEMBL1310547;15187_FLUKA;CTK3J6264;CNBUSIJNWNXLQQ-LLVKDONJSA-N;MolPort-000-861-443;(R)-N-(t-butoxycarbonyl)tyrosine;ZINC1576244;0947AC;ANW-35930
Boc-D-tyrosine is a D-configured tyrosine amino acid building block bearing a Boc-protecting group on the alpha-amino function, commonly used to control N-terminus reactivity during peptide assembly. Its side chain retains the phenolic hydroxyl characteristic of tyrosine, supporting downstream derivatization or controlled participation in coupling and post-synthetic functionalization workflows. As a protected amino acid, Boc-D-tyrosine is typically selected for stereochemically defined peptide segments where the D-configuration is required for conformational or stability considerations.
1. Stereodefined Peptide Segments
Boc-D-tyrosine is routinely used by custom peptide synthesis groups and medicinal chemistry laboratories to build stereochemically defined peptide sequences containing D-tyrosine residues. The Boc protection provides a controlled amino functionality for segment coupling strategies, while the preserved tyrosine phenol supports later handling depending on the target peptide design. Researchers often choose this specific protected, D-configured tyrosine building block when they need to introduce a D-amino acid to probe structure-activity relationships, influence local backbone conformation, or tune peptide properties during lead optimization.
2. Tyrosine Side-Chain Functionalization
Boc-D-tyrosine is leveraged in workflows that require post-assembly modification of the tyrosine side chain, since the phenolic hydroxyl enables derivatization without changing the peptide backbone stereochemistry. Peptide and bioconjugation development teams use D-tyrosine-containing intermediates to generate modified peptide constructs for chemical biology studies, including analogs where altered stereochemistry is used to evaluate how side-chain reactivity and presentation affect downstream performance. In these applications, the Boc-protected amino group helps maintain compatibility during peptide synthesis steps prior to side-chain conversion.
3. Pharmaceutical Intermediate Development
Boc-D-tyrosine is also used in pharmaceutical intermediate development for preparing defined D-tyrosine-containing fragments that feed into larger synthetic programs, including peptidomimetic and peptide-based intermediate libraries. Process chemists and R&D teams value the protected amino acid format because it supports controlled reactivity and reliable handling during multi-step synthesis where stereochemistry must be maintained. The tyrosine phenol provides a functional handle for subsequent transformations in the intermediate chain, enabling access to downstream building blocks used in medicinal chemistry campaigns.
2. The spatiotemporal control of signalling and trafficking of the GLP-1R
5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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