Boc-O-benzyl-D-tyrosine is a protected amino acid derivative in which the amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the carboxyl group is esterified as a benzyl ester, while the aromatic side chain of tyrosine is retained. The molecule bears the D-tyrosine stereochemical configuration as indicated by the "D" designation, and it contains a phenolic side-chain hydroxyl that remains unprotected, providing a polar hydrogen-bonding functional group alongside the protected α-amino and α-carboxyl functionalities. In peptide chemistry, this protected analogue is used as a stepwise building block precursor where Boc and benzyl ester protection support chemoselective transformations by reducing undesired reactivity of the α-functional groups during coupling and subsequent derivative assembly.
CAT No: CP02111
CAS No:63769-58-4
Synonyms/Alias:637337-65-6;(S)-3-(((Benzyloxy)carbonyl)amino)-2-methylpropanoicacid;Cbz-S-3-Aminoisobutyricacid;Cbz-S-3-Aminoisobutyricacid;Cbz-S-3-Aminoisobutyricacid;SCHEMBL6044100;CTK2F2636;MolPort-023-331-656;ZINC2389774;ANW-63290;(S)-3-(N-Cbz-amino)isobutyricacid;AKOS015911840;AJ-35616;AK-87765;SC-10103;KB-211290;TC-152035;I14-37366;Propanoicacid,2-methyl-3-[[(phenylmethoxy)carbonyl]amino]-,(2S)-
Boc-O-benzyl-D-tyrosine is a D-tyrosine derivative bearing a Boc-protected amino group and an O-benzyl-protected phenolic side chain, providing orthogonal protection for controlled peptide assembly. The D-configuration at the amino acid backbone supports stereochemically defined incorporation into peptides and peptidomimetics, while the protected phenol minimizes side reactions during coupling and deprotection workflows. This protected amino acid building block is commonly selected when researchers need tyrosine functionality masked for synthesis, with the stereocenter preserved through downstream fragment assembly.
1. D-Tyrosine Peptide Building Block
Boc-O-benzyl-D-tyrosine is used as a protected amino acid building block for assembling D-tyrosine-containing peptides by both solid-phase and solution-phase strategies. Peptide chemists rely on the Boc group to manage N-terminus reactivity during stepwise coupling, while the O-benzyl protection suppresses phenolic side reactions that can otherwise complicate fragment condensation. Incorporation of the D-tyrosine stereochemistry is particularly valuable in peptide library construction and structure-activity relationship studies where stereochemical control is required for conformational effects and protease-resistance screening in chemical biology workflows.
2. Peptidomimetic And SAR Studies
Boc-O-benzyl-D-tyrosine supports the synthesis of peptidomimetics and stereochemically defined analogs used in medicinal chemistry research. In SAR campaigns, D-amino acid substitution is frequently employed to probe how backbone stereochemistry and side-chain presentation affect binding-site recognition and overall scaffold behavior, and the protected tyrosine phenol helps maintain synthetic fidelity during iterative functional group installation. By carrying a masked phenolic oxygen, this derivative enables downstream generation of tyrosine-derived functionality under controlled conditions after the peptide or peptidomimetic scaffold is assembled.
3. Protected Segment Condensation
Boc-O-benzyl-D-tyrosine is frequently selected for segment condensation and complex fragment assembly where orthogonal protection and side-chain suppression are critical. In multi-step peptide synthesis, the protected phenolic oxygen reduces the risk of undesired crosslinking, oxidation, or side reactions that can occur with free tyrosine under coupling and activation conditions. The Boc-protected amino group also aligns with workflows that require controlled deprotection timing between synthetic steps, making this derivative a practical choice for constructing longer sequences or densely functionalized peptide fragments in research-grade custom synthesis.
4. Pharmaceutical Intermediate Development
Boc-O-benzyl-D-tyrosine is used as a stereochemically defined protected intermediate for downstream manufacture of tyrosine-containing building blocks and related protected fragments used in pharmaceutical intermediate development. Process and development chemists value the masked phenolic functionality because it improves handling and reduces side reactions during intermediate transformations that occur prior to final deprotection or functionalization. This derivative's D-stereochemistry is especially relevant when the target intermediate must retain a specific stereochemical configuration for later coupling into larger molecules, including advanced peptide-like scaffolds and tyrosine-derived synthetic intermediates.
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