D-Tyrosine is the D-stereoisomer of the proteinogenic amino acid tyrosine, featuring an aromatic phenyl side chain bearing a phenolic hydroxyl group attached to the alpha carbon. The molecule contains both an amino group and a carboxyl group, and its phenolic functionality can participate in hydrogen bonding and can be chemically modified under conditions used for phenol derivatization while the D-configuration distinguishes it from the L form in stereochemical recognition. In biochemical and peptide chemistry workflows, D-Tyrosine is used as a stereochemically defined building block for preparing D-containing peptides and for structure-activity or labeling studies where the aromatic phenol handle and the non-native stereochemistry are relevant.
CAT No: CP02101
CAS No:556-02-5
Synonyms/Alias:Z-DL-Lys(Z)-OH;55592-85-3;2,6-Bis(((benzyloxy)carbonyl)amino)hexanoicacid;55592-85-3[rn];2,6-di{[(benzyloxy)carbonyl]amino}hexanoicacid;Nalpha,Nepsilon-Di-Z-DL-lysine;NSC88474;AC1Q5SJP;ACMC-209u7a;AC1L3ZY6;N|A,N|A-Di-Z-DL-lysine;96837_ALDRICH;SCHEMBL806151;AC1Q71R3;96837_FLUKA;CTK5A3858;N-Alpha,epsilon-bis-Z-DL-lysine;BLZXFNUZFTZCFD-UHFFFAOYSA-N;MolPort-001-788-386;N2,N6-Dibenzyloxycarbonyl-L-lysine;EINECS206-971-9;AR-1G6896;NSC-88474;AKOS016846183;N2,N6-bis[(benzyloxy)carbonyl]lysine
D-Tyrosine is the D-enantiomer of the canonical amino acid tyrosine, featuring a chiral α-carbon bearing an amino group and a carboxylic acid, plus a phenolic side chain on the aromatic ring. The stereochemical inversion relative to L-tyrosine makes it a useful chiral building block for stereodefined peptide and peptidomimetic chemistry where D-amino acid incorporation can alter backbone conformation and protease stability. The phenolic hydroxyl enables selective protection and subsequent functional group transformations, while the amino and carboxyl groups support standard peptide coupling and downstream derivatization. As a free amino acid, D-Tyrosine participates in salt formation, esterification, and N- or O-protection strategies that control chemoselectivity during synthesis of protected amino acid derivatives and analytical standards.
1. Peptide Synthesis
D-Tyrosine serves as a D-amino acid building block for peptide coupling chemistry in solid-phase or solution-phase workflows, where the amino and carboxyl functionalities enable formation of amide bonds with activated carboxylic acid derivatives. The phenolic side chain can be protected as an ether or carbonate during chain assembly, supporting orthogonal deprotection to reveal the native tyrosine hydroxyl at a defined stage. Incorporation of the D-configuration allows stereochemically defined analogs for peptide library construction, including backbone-modified sequences used in structure-activity relationship studies. D-Tyrosine also functions as a starting point for converting to protected D-tyrosine derivatives that are compatible with common coupling reagents and peptide purification strategies.
2. Peptidomimetics And SAR
D-Tyrosine is utilized in peptidomimetic design and SAR studies where aromatic, phenolic side-chain chemistry is leveraged alongside D-stereochemistry to modulate binding interactions and metabolic stability. The tyrosine phenol can be selectively functionalized through O-alkylation, O-acylation, or oxidative transformations to generate analogs that probe hydrogen-bonding patterns and aromatic positioning in target-binding pockets. The free amino acid framework can be converted into N-protected, C-activated, or side-chain-protected forms to support systematic analog synthesis while maintaining stereochemical integrity at the α-center. Downstream derivatives prepared from D-Tyrosine can be used to generate structure-defined molecular scaffolds for medicinal chemistry optimization and conformational mapping.
3. Chemical Biology Labeling
D-Tyrosine supports chemical biology workflows that require stereochemically defined aromatic amino acid handles for biomolecule modification and detection chemistry. The phenolic hydroxyl provides a functional group for conjugation-compatible transformations, including formation of activated esters or ether-linked motifs after appropriate protection/deprotection control. The amino acid backbone can be incorporated into peptide tags or protein fragments, enabling site-specific labeling strategies that distinguish D-amino acid-containing constructs from native L-tyrosine. Resulting labeled peptides or conjugates can be used in biochemical assays, binding studies, or analytical characterization where stereochemistry and side-chain functionality influence molecular recognition.
4. Protected Amino Acid Chemistry
D-Tyrosine is applied as a chiral starting material for producing protected amino acid derivatives used in protected amino acid synthesis and intermediate preparation. The amino group can be N-protected to suppress side reactions during activation of the carboxyl group, while the phenolic hydroxyl can be protected to control chemoselectivity during multi-step sequences. The D-configuration provides stereochemical fidelity that is retained through standard protection, activation, and coupling steps, enabling reliable construction of D-tyrosine-containing peptides and analogs. Protected forms derived from D-Tyrosine can serve as processable intermediates for fine chemical synthesis, including C-terminal modification and side-chain functionalization routes.
5. Analytical Standards and Method Development
D-Tyrosine is suitable for analytical research and method development where enantiomeric discrimination between D- and L-tyrosine is required for amino acid profiling, stereochemical purity assessment, or tracer studies. The defined aromatic phenol and α-amino acid functionality make it compatible with derivatization strategies used in chromatographic detection, including fluorescence or mass spectrometric workflows after appropriate functional group activation. Stereochemically defined D-tyrosine standards can also be employed to validate sample preparation steps for peptide hydrolysates and to support calibration in quantitative amino acid analyses. Analytical use of D-Tyrosine aligns with broader amino acid chemistry practices that require chiral reference materials for robust, interpretable measurements.
6. Pharmaceutical Intermediate Preparation
D-Tyrosine is employed in pharmaceutical intermediate preparation and process chemistry contexts where D-amino acid motifs are introduced into peptide-like or peptidomimetic structures during synthesis of research-grade candidates. The amino acid's functional groups enable transformation into activated carboxyl derivatives and N-protected building blocks that can be coupled under controlled conditions to construct defined amide linkages. Phenolic side-chain chemistry allows downstream generation of protected or functionalized tyrosine analogs that can be carried through manufacturing steps with predictable deprotection behavior. D-Tyrosine-derived intermediates can therefore support specialty chemical production routes that require stereochemically consistent chiral building blocks for scalable peptide and peptidomimetic synthesis.
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