3-Chloro-DL-tyrosine

3-Chloro-DL-tyrosine is a tyrosine-derived amino acid featuring a chloro substituent on the aromatic ring, supplied as a DL mixture of stereoisomers at the alpha-carbon. The phenolic side chain and the amino acid functionality make it a practical aromatic amino acid building block for chemical synthesis and analytical method development, while the aryl chloride provides a handle for downstream functionalization. Researchers typically select this reagent when they need an electrophile-bearing tyrosine analog for derivatization, labeling, or incorporation into custom peptide and small-molecule intermediates.

1. Aromatic Derivatization

3-Chloro-DL-tyrosine is used by organic and medicinal chemistry groups to introduce an aryl-chloride functionality onto tyrosine-like scaffolds for subsequent coupling, substitution, or stepwise elaboration. The combination of a phenolic side chain with a chloro-substituted aromatic ring supports workflows where tyrosine-derived motifs are modified to tune reactivity for library synthesis, SAR-focused intermediate generation, or reference compound preparation. Because the reagent is supplied as a DL mixture, it is commonly chosen for synthetic campaigns where stereochemical purity at the alpha-carbon is not the primary requirement and where the downstream target is defined by transformations on the aromatic ring.

2. Peptide And Peptidomimetic Building Block

3-Chloro-DL-tyrosine is applied as an amino acid building block for preparing tyrosine-containing peptides and peptidomimetic structures in research and custom synthesis settings. The aromatic ring substitution pattern enables incorporation of a halogenated phenylalanine/tyrosine-like residue into sequence-defined constructs that are later functionalized or used as probes for chemical reactivity studies. This product format is particularly relevant when the project focuses on the presence of the aryl chloride and phenolic group for downstream derivatization rather than on stereochemically pure alpha-amino acid incorporation.

3. Chemical Biology Labeling Probes

3-Chloro-DL-tyrosine is used in chemical biology workflows to generate tyrosine-based labeling reagents and probe precursors that rely on an aryl chloride as a reactive handle. The phenolic group supports further derivatization to attach detection tags, affinity motifs, or reporter groups, while the chloro substituent provides a defined functional element for subsequent conjugation or synthetic diversification. Laboratories developing small-molecule probes, affinity reagents, or derivatized aromatic amino acid standards often select this reagent when a tyrosine scaffold with a built-in electrophilic aromatic position is required for controlled downstream assembly.

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