Fmoc-[15N]Tyr-OH

Fmoc-[15N]Tyr-OH is an Fmoc-protected, 15N-labeled tyrosine derivative in which the amino acid backbone bears a chiral α-carbon and the nitrogen atom is enriched for stable-isotope tracing. The structure combines an Fmoc carbamate on the amino group with a free carboxylic acid and a phenolic side chain, enabling both peptide coupling chemistry and site-specific functional readouts. The labeled 15N nucleus provides strong discrimination in isotope-resolved mass spectrometry and NMR-based workflows, while the phenol can participate in controlled derivatization or remain protected during peptide assembly. The compound therefore functions as a chiral, isotope-tagged amino acid building block and biochemical research intermediate compatible with standard protected amino acid strategies.

1. Isotope-Labeled Peptide Synthesis

Fmoc-[15N]Tyr-OH supports peptide building block preparation for isotope-resolved studies by pairing an Fmoc-protected amine with a free carboxyl group for coupling under Fmoc-based solid-phase or solution-phase peptide synthesis conditions. The tyrosine side chain phenol can be managed through orthogonal protection choices so that the labeled nitrogen remains the primary isotopic handle during synthesis and purification. Incorporation of the [15N]tyrosine residue enables unambiguous tracking of backbone connectivity and residue-specific dynamics in peptide and protein fragments. Downstream, labeled peptides prepared from this amino acid can serve as standards for analytical method development and as probes for mechanistic interpretation in peptide science.

2. Protein Engineering Studies

Fmoc-[15N]Tyr-OH is suitable for protein engineering research workflows that require residue-specific isotope labeling of tyrosine to interrogate structural and interaction changes at the amino acid level. The chiral tyrosine architecture and the phenolic side chain enable faithful incorporation into peptide segments that mimic native sequence context, while the 15N label provides a spectroscopic signature for monitoring local environments. Fmoc protection allows controlled assembly of labeled domains, and the free carboxylic acid supports incorporation into larger constructs through standard peptide coupling chemistry. The resulting isotope-tagged peptides or protein fragments can be applied to mapping conformational effects, validating computational models, and supporting residue-level structure-function analyses.

3. Mass Spectrometry Standards

Fmoc-[15N]Tyr-OH functions as an isotope-labeled reference material for analytical research in which [15N] enrichment improves assignment confidence for tyrosine-containing peptides. The Fmoc group and carboxylic acid allow the compound to be incorporated into defined peptide sequences that generate interpretable isotope patterns upon fragmentation in LC-MS/MS workflows. The phenolic side chain can be derivatized or kept under controlled conditions depending on the analytical target, enabling consistent behavior across method development and validation. Downstream use includes calibrant preparation, isotope-resolved quantitation strategies, and confirmation of peptide identity in complex mixtures where tyrosine-containing fragments are common.

4. Side-Chain Functionalization Chemistry

Fmoc-[15N]Tyr-OH enables side-chain functionalization strategies that leverage the tyrosine phenol for controlled derivatization while retaining an isotope label for traceability. The phenolic hydroxyl can undergo selective transformations such as etherification, conjugation handle installation, or oxidative coupling routes, and the labeled backbone nitrogen provides a persistent marker through downstream processing. Fmoc protection supports orthogonal handling during multistep synthesis, allowing side-chain modification without perturbing the amino acid's coupling-ready functionality until desired. The resulting labeled tyrosine derivatives can be used to generate functionalized peptide analogs, study chemical reactivity patterns, or prepare isotope-tagged intermediates for further synthetic elaboration.

5. Process Chemistry Intermediate

Fmoc-[15N]Tyr-OH serves as a chiral, isotope-labeled amino acid intermediate for fine chemical synthesis and process chemistry where reproducible building block performance is required. The combination of Fmoc-protected amine and free carboxylic acid supports standardized protection/deprotection logic and predictable peptide-coupling compatibility across manufacturing-relevant synthetic routes. The stable 15N label is retained through typical Fmoc deprotection and coupling steps, enabling consistent downstream labeling for manufacturing of isotope-tagged peptide reagents. The compound can be employed to prepare labeled materials for analytical supply chains, research reagent production, and isotope-enabled synthetic workflows that demand traceable amino acid incorporation.

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