H-[15N]Ala-OH

H-[15N]Ala-OH is an isotopically labeled alanine bearing a 15N atom at the amino nitrogen, retaining the native alpha-amino acid skeleton with a free carboxylic acid and an unprotected amino functionality. The stereocenter at the alpha carbon corresponds to L-alanine configuration, which is critical for recognition by peptide coupling reagents and for alignment with stereochemical requirements in amino acid incorporation workflows. The labeled amine and acid groups provide a defined reactivity profile for standard amino acid chemistry, including salt formation, activation for peptide bond formation, and downstream derivatization into amides, esters, or protected intermediates. The 15N enrichment enables isotope-resolved spectroscopic tracking of nitrogen-containing fragments in peptide and protein-related studies, making the compound a direct research intermediate for labeled building blocks.

1. Isotope Labeling Studies

H-[15N]Ala-OH is used in isotope labeling workflows for NMR and mass spectrometry studies that require unambiguous tracking of alanine-derived nitrogen in complex biomolecular assemblies. The 15N-labeled amino group allows nitrogen-specific signal assignment in peptide fragments, while the free carboxyl group supports conversion into activated derivatives for incorporation into larger structures. The L-configuration supports stereochemically consistent incorporation during peptide coupling or enzymatic processing, enabling interpretation of site-specific labeling patterns. Labeled alanine can be employed to generate defined isotopologue distributions for mechanistic studies, fragment mapping, and nitrogen transfer observation in biochemical research intermediate preparation.

2. Peptide Synthesis Incorporation

H-[15N]Ala-OH serves as an alanine building block for peptide coupling chemistry where nitrogen labeling is required at a specific residue position. The free amino and carboxylic acid functionalities can be transformed into peptide-ready forms through standard protection and activation strategies, supporting amide bond formation at the alpha-carboxyl group while maintaining the labeled nitrogen. The stereogenic alpha carbon enables incorporation with correct stereochemistry, which is essential for peptide conformational fidelity and for avoiding epimerization during synthesis planning. The resulting 15N-containing peptide analogs can be used for residue-resolved structural studies, peptide library construction, and analytical method development for isotope-resolved characterization.

3. Protein Engineering Tracing

H-[15N]Ala-OH is applied in protein engineering and chemical biology contexts that benefit from site-specific nitrogen labeling to monitor local dynamics and interaction pathways. The alanine side chain is minimal, which reduces spectral complexity and helps isolate backbone or local nitrogen contributions when the labeled residue is incorporated. The carboxylate and amino groups enable conversion into protected amino acid derivatives or coupling partners that can be used to introduce the labeled residue into peptide segments used in protein domain assembly. The isotopic handle can be exploited for nitrogen-sensitive readouts in structural characterization, conformational analysis, and interaction mapping across engineered biomolecule constructs.

4. Analytical Research Standards

H-[15N]Ala-OH is utilized as a reference material for analytical research requiring isotope-resolved quantification of alanine and alanine-containing fragments. The 15N-labeled nitrogen provides a distinct mass shift and nitrogen-specific spectroscopic signature, while the intact amino acid functionality supports preparation of calibration solutions, derivatized standards, and labeled internal controls. The free acid form supports consistent handling in chromatographic workflows and enables formation of salts or derivatization products that mimic sample matrices. The labeled standard can be employed to validate labeling efficiency in peptide synthesis workflows and to support method transfer for nitrogen-targeted LC-MS and NMR analyses.

5. Fine Chemical Intermediate Conversion

H-[15N]Ala-OH functions as a chiral amino acid intermediate for downstream synthesis of protected amino acid derivatives and nitrogen-labeled building blocks used in synthetic organic chemistry. The presence of both amino and carboxylic acid groups enables selective functional group transformations, including protection of the amine and activation or esterification of the acid to create coupling-ready intermediates. The L-alanine stereochemistry can be preserved through appropriate protection-group strategies, supporting stereochemically controlled manufacturing routes for labeled fine chemicals. The resulting labeled intermediates can feed into peptide fragment preparation, isotopically labeled amide/ester synthesis, and process chemistry intermediate generation for research-grade production of nitrogen-traceable molecules.

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