H-[15N]Tyr-OH is a free, isotopically labeled tyrosine amino acid derivative in which the backbone nitrogen is enriched with 15N while the molecule retains the phenolic aromatic side chain characteristic of tyrosine. The structure contains an amino group and a carboxylic acid functional group (both unprotected), and the side chain bears a para-hydroxyl substituent that can participate in hydrogen bonding and acid-base behavior typical of phenolic groups. H-[15N]Tyr-OH is used as an isotopic tracer and labeled substrate for amino acid and peptide-related analytical studies, including mass spectrometry method development and incorporation of the labeled residue into synthetic peptide targets for structural or labeling experiments.
H-[15N]Tyr-OH is an isotopically labeled tyrosine containing a ^15N atom at the amino nitrogen of the amino acid backbone, retaining the native L-configuration at the α-carbon. The molecule features a free carboxylic acid (-CO2H), a free primary amine (-^15NH2), and a phenolic side chain (-OH) on the aromatic ring, enabling both acid-base chemistry and phenol-directed derivatization. Tyrosine's aromatic phenol can participate in electrophilic aromatic substitution, oxidative coupling, and selective protection strategies, while the amino and carboxyl groups support standard peptide coupling and deprotection logic. As a chiral, N-labeled amino acid, H-[15N]Tyr-OH functions as a biochemical research intermediate and an NMR/labeling reagent for tracking tyrosine-containing species across synthetic and analytical workflows.
1. Peptide Synthesis
H-[15N]Tyr-OH supports peptide building workflows where tyrosine residues must be incorporated with defined ^15N labeling at the backbone amide position. The free α-amino and α-carboxyl functionality can be converted into coupling-ready forms compatible with standard peptide coupling chemistries, while the phenolic -OH can be temporarily protected to prevent side reactions during amide bond formation. The L stereochemistry is preserved through amino acid handling, enabling stereochemically consistent incorporation into peptide chains and downstream fragment assembly. ^15N labeling at the amino nitrogen enables tracking of the resulting tyrosine-containing peptide segments by isotope-sensitive spectroscopy and mass spectrometric workflows, supporting labeled peptide preparation for structural and mechanistic studies.
2. Chemical Biology Labeling
H-[15N]Tyr-OH is suitable for chemical biology research that requires isotopically defined tyrosine analogs to monitor protein or peptide behavior. The phenolic side chain can be used to generate tyrosine-specific derivatives, including protected forms for controlled conjugation or functionalization, while the labeled backbone nitrogen provides an observable tag for isotope-resolved detection. The combination of an aromatic phenol and a ^15N-labeled amine enables studies that distinguish tyrosine-containing intermediates, digestion products, or binding partners in complex mixtures using isotope-sensitive analytical methods. Labeled amino acid chemistry using H-[15N]Tyr-OH can therefore feed into mechanistic probes and biomolecular characterization pipelines where tyrosine identity and nitrogen labeling are simultaneously required.
3. Protein Engineering Studies
H-[15N]Tyr-OH can be employed in protein engineering and protein characterization contexts where tyrosine positions are interrogated with isotope-resolved readouts. The compound's chiral amino acid framework allows incorporation into tyrosine-containing sequences during labeled protein or peptide preparation, while the phenolic group can be protected or derivatized to model post-translational modification states or to control reactivity during synthesis. The ^15N label at the backbone nitrogen provides a spectroscopic handle for mapping local environments around tyrosine-derived amide units in peptide fragments and assembled proteins. Downstream use includes generation of labeled protein fragments for structural analysis, interaction mapping, and comparative studies of tyrosine-dependent conformational or binding effects.
4. Analytical Research Standards
H-[15N]Tyr-OH functions as an analytical research standard and calibration component for isotope-resolved quantification of tyrosine-containing analytes. The labeled nitrogen provides distinguishable mass and isotope signatures, enabling targeted detection of tyrosine derivatives, peptide fragments, and digestion products that contain the ^15N-labeled amide nitrogen. The presence of both carboxylic acid and phenolic hydroxyl groups supports controlled derivatization into stable analytical forms, improving compatibility with chromatographic separation and detector response. Use of H-[15N]Tyr-OH in analytical method development supports robust identification and quantitation of labeled amino acid species and tyrosine-containing peptide motifs in biochemical workflows.
5. Protected Amino Acid Derivatives
H-[15N]Tyr-OH serves as a starting material for protected amino acid derivative synthesis where orthogonal protection strategies are required for peptide-compatible chemistry. The α-amino group can be converted to N-protected forms for selective peptide coupling, while the phenolic -OH can be protected to suppress oxidative side reactions and to enable controlled deprotection at the appropriate synthetic stage. The free carboxylic acid can be transformed into activated ester or coupling-ready intermediates, supporting C-terminal modification logic and fragment assembly. Isotopic integrity of the ^15N label is maintained through protection/deprotection sequences, making the resulting protected ^15N-tyrosine derivatives suitable for labeled peptide building block preparation and downstream isotope-resolved characterization.
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