DL-Homotyrosine.HBr is a free amino acid derivative in which the side chain is an extended phenolic analog of tyrosine, featuring a benzene ring bearing a hydroxy group and an additional methylene unit relative to the parent amino acid. The molecule contains an amino group and a carboxyl group, and it is provided as a hydrobromide salt, with the bromide counterion associated to the protonated amine; the "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon. In peptide and amino acid chemistry workflows, the phenolic side chain enables derivatization and conjugation strategies, while the salt form supports handling and solubility for solution-phase or solid-phase incorporation into protected amino acid building blocks and related analytical or structure-activity studies.
CAT No: CP18602
DL-Homotyrosine.HBr is a bromide salt form of the amino acid homotyrosine, corresponding to a phenolic aromatic side chain extended by one methylene relative to tyrosine. The molecule contains a stereogenic center at the alpha carbon, and the DL designation indicates a racemic mixture that can be resolved downstream or used directly for non-stereospecific synthesis. Protonated amino functionality paired with the phenolic hydroxyl enables acid-base controlled reactivity, while the aromatic ring supports electrophilic substitution and coupling chemistry after appropriate functional group management. As an amino acid building block and chiral synthetic precursor, DL-Homotyrosine.HBr can be converted into protected amino acid derivatives and peptide-compatible intermediates for C-terminal or side-chain functionalization workflows.
1. Peptide Synthesis
DL-Homotyrosine.HBr is applied in peptide building block preparation where homotyrosine's amino acid backbone participates in standard peptide coupling chemistry after conversion to an N-protected form. The phenolic hydroxyl on the extended aromatic side chain can be protected as an ether or carbonate to prevent side reactions during amide bond formation, while the alpha-carboxyl group can be activated for coupling or esterified for controlled transformations. Racemic stereochemistry is often acceptable for screening libraries, peptide analog generation, or method development where stereochemical purity is not the primary variable. Downstream, protected DL-homotyrosine derivatives can be incorporated as residues in peptide synthesis to generate side-chain-modified sequences for biochemical research and material-science peptide constructs.
2. Side-Chain Functionalization
DL-Homotyrosine.HBr is suitable for side-chain functionalization strategies that exploit the phenolic hydroxyl and the aromatic ring for controlled derivatization. The phenolic group can be selectively protected and later deprotected to enable phosphorylation-mimetic chemistry, ether formation, or aromatic coupling reactions that introduce handles for further conjugation. The extended side chain length relative to tyrosine can influence spacing in multivalent constructs, supporting design of linkers in bioconjugation and peptidomimetic scaffolds. Resulting functionalized homotyrosine derivatives can serve as intermediates for labeled probes, affinity reagents, or polymer-bound phenolic motifs used in applied chemical research.
3. Chiral Resolution Intermediates
DL-Homotyrosine.HBr functions as a practical chiral amino acid intermediate for workflows that begin with racemic material and proceed to stereochemical separation. The presence of the amino acid salt form and the phenolic hydroxyl enables formation of diastereomeric derivatives with chiral acids or chiral auxiliaries, after which enantiomerically enriched homotyrosine derivatives can be recovered for stereodefined synthesis. The alpha stereocenter can then be carried through into protected amino acid derivatives, allowing downstream peptide construction with defined stereochemistry at the residue. Industrially, this approach supports process design for chiral fine chemical synthesis where racemate handling and later resolution can be integrated into manufacturing routes.
4. Chemical Biology Probes
DL-Homotyrosine.HBr can be employed in chemical biology research to generate phenol-bearing amino acid derivatives used for labeling, immobilization, and molecular recognition studies. The amino acid functionality supports conversion to protected intermediates that enable incorporation into peptides, while the phenolic hydroxyl provides a reactive site for attachment of linkers, fluorophores, or affinity tags under protection/deprotection control. Racemic use may be appropriate for mapping binding tolerance, optimizing assay reagents, or producing mixed stereochemical standards for analytical method development. Downstream derivatives derived from DL-homotyrosine can be used to construct probe libraries and biomolecule conjugates where aromatic phenol chemistry is a key recognition element.
5. Pharmaceutical Intermediate Preparation
DL-Homotyrosine.HBr is relevant to pharmaceutical intermediate preparation where amino acid-derived fragments are incorporated into peptidomimetic or small-molecule scaffolds. The protected amino acid chemistry compatible with amide bond formation enables conversion into N-protected, side-chain-protected intermediates that can be coupled to carboxylic acids or activated esters during synthetic assembly. The phenolic hydroxyl can be managed through protection strategies to control reactivity during multistep routes, then selectively unmasked for late-stage functionalization or conjugation. Industrial fine chemical synthesis can therefore use DL-homotyrosine-based intermediates as feedstock for structurally defined building blocks that support medicinal chemistry programs and process-scale production of amino acid-derived entities.
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