3,5-Dichloro-D-tyrosine is a halogenated, non-proteinogenic tyrosine analogue in which two chlorine atoms substitute the aromatic ring at the 3 and 5 positions, and the amino acid is specified as the D stereoisomer. The molecule contains a primary amino group and a carboxylic acid functional group, with a phenolic side chain that is retained but electronically modified by the ortho/para halogen substitution pattern, affecting its acidity and aromatic reactivity relative to unmodified tyrosine. As a structurally defined D-amino acid building block, it is used in peptide and conjugate synthesis and in chemical biology or analytical studies where halogenated aromatic residues and stereochemical control are required for structure-activity investigations, labeling strategies, or mass spectrometric method development.
CAT No: CP18002
3,5-Dichloro-D-tyrosine is a halogenated D-tyrosine derivative featuring two chlorine atoms on the phenolic ring and a D-configured amino acid backbone. The activated phenolic substitution pattern and the non-proteinogenic stereochemistry make it a useful building block for preparing halogen-rich aromatic motifs in peptide and medicinal chemistry workflows. Researchers often select this scaffold when they need defined aromatic electronics and steric effects from ring dichlorination while maintaining a stereochemically controlled amino acid unit for downstream coupling or analytical reference preparation.
1. Halogenated Peptide Building Blocks
3,5-Dichloro-D-tyrosine is used as a specialty amino acid building block for assembling peptides and peptidomimetic structures that incorporate a D-tyrosine motif. Peptide synthesis groups value the 3,5-dichloro substitution because it provides a strongly defined aromatic environment that can influence conformational preferences and chemical reactivity of the tyrosine-derived side chain during peptide construction. This product is particularly relevant for custom peptide synthesis and structure-activity relationship (SAR) studies where researchers need consistent incorporation of a halogenated aromatic residue rather than relying on natural tyrosine. The D-configuration supports workflows aimed at generating stereochemically defined analogs for protease-stability and structure probing studies, where stereochemistry control is a key design parameter.
2. Medicinal Chemistry SAR Intermediates
3,5-Dichloro-D-tyrosine serves as a practical intermediate for medicinal chemistry programs that require halogenated phenylalanine/tyrosine-like aromatic units in small-molecule or peptide-small-molecule hybrid scaffolds. Medicinal chemistry and process development teams use this reagent to introduce a dichlorinated aromatic ring that can modulate physicochemical properties such as hydrophobicity and electronic character, while the D-configuration enables stereochemically defined analog series. In downstream synthesis, the amino acid functionality provides a reliable handle for coupling into larger frameworks, supporting the rapid preparation of analog libraries used in lead optimization and chemical biology probe development. The distinct ring substitution pattern also helps ensure reproducibility when comparing compounds across SAR campaigns.
3. Chemical Biology Probe Design
3,5-Dichloro-D-tyrosine is applied in chemical biology workflows that require tyrosine-derived aromatic residues with enhanced halogen content for labeling, affinity reagent construction, or probe scaffolds. Researchers often incorporate this amino acid into peptide-based probes to create defined aromatic binding surfaces or to tune noncovalent interactions through the 3,5-dichloro pattern, while the D-configuration supports probe designs that aim to reduce ambiguity from stereochemical variation. This reagent is therefore commonly used by groups building customized probe molecules for target engagement studies, binding assays, or mechanistic experiments where the aromatic side chain identity must be tightly controlled. Its role is typically to provide a stereodefined, halogenated aromatic element that can be carried through to the final probe format with minimal structural drift.
4. Analytical Reference Standards
3,5-Dichloro-D-tyrosine is also used as an analytical reference material in method development and characterization workflows involving halogenated amino acid motifs. Analytical chemistry teams employ this compound to support LC-MS identification and retention behavior checks for dichlorinated tyrosine analogs and related peptide fragments, especially when monitoring synthetic intermediates or final products that contain the 3,5-dichloro aromatic signature. Because the stereochemistry is explicitly defined, it can be valuable for distinguishing D-configured derivatives from closely related tyrosine species during analytical method validation and impurity profiling. This application is particularly relevant for laboratories working on peptide analog synthesis, halogenated metabolite or fragment studies, and quality control of specialized amino acid-containing building blocks.
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