H-Tyr(SO3H)-OH

H-Tyr(SO3H)-OH is a tyrosine-derived amino acid bearing a phenolic side chain substituted with a sulfonic acid group, combining an amino acid backbone with a strongly acidic, water-solubilizing sulfonate functionality. The molecule exists as a chiral amino acid intermediate at the α-carbon (with stereochemistry inherited from the tyrosine configuration), and it presents a free carboxylic acid and a free amino group that can participate in coupling or salt formation. The sulfonic acid substituent is typically retained under many peptide-coupling conditions and can influence ion pairing, conformational preferences, and chromatographic behavior. The presence of a phenol-to-sulfonate motif enables downstream derivatization into sulfonated aromatic residues used in peptide and biomolecule chemistry, as well as in analytical and process-oriented intermediate synthesis.

1. Peptide Synthesis

H-Tyr(SO3H)-OH is applied in peptide building and residue incorporation workflows where a sulfonated tyrosine analog is needed to model or introduce anionic side-chain character. The amino acid backbone supports standard peptide coupling strategies through the α-amino and α-carboxyl functions, while the sulfonic acid group on the aromatic ring can be used to tune solubility and electrostatic interactions in the resulting peptide. Protecting-group planning can leverage the stability of sulfonic acids relative to many phenolic protecting groups, enabling selective protection of the α-amino or α-carboxyl to control chemoselectivity during assembly. The resulting sulfonated aromatic peptides can serve as substrates, reference materials, or structure probes in peptide science and amino acid chemistry.

2. Chemical Biology

H-Tyr(SO3H)-OH supports chemical biology applications that require an anionic tyrosine mimic for studying recognition processes involving negatively charged aromatic motifs. The sulfonate-bearing phenyl ring can participate in electrostatic and hydrogen-bonding interactions, while the α-amino acid framework enables conversion into labeled or conjugatable derivatives. Derivatization can be directed toward forming peptide conjugates, affinity handles, or immobilized ligands where the sulfonate group maintains strong charge under a wide pH range. Downstream use includes generating molecular probes for mapping binding preferences and for constructing biomolecule-modified systems with defined sulfonated aromatic chemistry.

3. Bioconjugation

H-Tyr(SO3H)-OH is suitable for bioconjugation and biomolecule modification strategies that rely on introducing a sulfonated aromatic residue into larger constructs. The free carboxylic acid and amino group can be transformed into activated intermediates for amide formation or for coupling into carrier proteins, polymers, or linkers, while the sulfonate group provides persistent negative charge that can affect conjugate solubility and surface charge. Selective protection of the amino or carboxyl functionality can help maintain the sulfonate group during conjugation steps and improve control over coupling stoichiometry. The resulting sulfonated conjugates can be employed as analytical standards, reagent components, or charge-defined materials in applied biochemical research.

4. Analytical Research

H-Tyr(SO3H)-OH functions as an analytical reference and calibration component for methods targeting sulfonated tyrosine species and related amino acid derivatives. The combination of amino acid functionality and a strongly acidic sulfonate group yields predictable ionization behavior, supporting LC-MS and electrophoretic analyses that distinguish sulfonated aromatic residues from non-sulfonated analogs. The chiral α-carbon can also be leveraged when enantiomeric separation or stereospecific quantification of tyrosine-derived sulfonates is required. Downstream formation of labeled or derivatized standards can further enable method validation for amino acid derivatization, metabolite profiling, and process monitoring in fine chemical synthesis.

5. Process Chemistry Intermediate

H-Tyr(SO3H)-OH is used as a chiral amino acid intermediate in process chemistry and specialty chemical production where sulfonated aromatic building blocks are required. The molecule's stable sulfonic acid functionality can remain intact while the α-amino and α-carboxyl groups are selectively protected or activated to fit manufacturing routes for protected amino acid derivatives and peptide coupling partners. Salt formation and pH-controlled handling can be integrated into downstream purification and crystallization steps, leveraging the high polarity of the sulfonate group. The compound can serve as a feedstock for generating sulfonated tyrosine-containing intermediates used in peptide analog construction, biochemical reagent manufacture, and other industrial fine chemical applications.

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