Fmoc-[15N]Ala-OH is an Fmoc-protected alanine derivative bearing an isotopically labeled [15N] atom at the amino nitrogen, classifying it as a protected, isotopically labeled amino acid suitable for peptide chemistry. The molecule contains a free carboxylic acid (-COOH) while the α-amino group is protected as an Fmoc carbamate, and the labeled nitrogen provides a defined isotopic signature for mass spectrometric or NMR-based tracking. In synthesis and analytical workflows, it is used as a stepwise building block for preparing peptides or peptide intermediates where controlled incorporation of a labeled alanine residue is required for structure-activity studies, isotopic labeling, or method development.
CAT No: CP26226
CAS No:117398-49-9
Synonyms/Alias:Fmoc-Ala-OH(15N);117398-49-9;FmoC-[15N]Alanine;Fmoc-Ala-OH-15N;L-Alanine-15N,N-Fmoc;489905_ALDRICH;CTK8F9901;9951AC;N-(9-Fluorenylmethoxycarbonyl)-L-alanine-15N
Fmoc-[15N]Ala-OH is an N-fluorenylmethoxycarbonyl (Fmoc) protected alanine bearing an isotopically labeled amine nitrogen at the [15N] position, with the stereogenic center corresponding to L-alanine configuration. The molecule contains the Fmoc carbamate on the amino nitrogen and a free carboxylic acid, creating a protected amino acid building block compatible with standard peptide coupling workflows while preserving the labeled backbone for spectroscopic tracking. The [15N] label provides a distinct isotope signature for NMR, MS, and mass-dependent fragmentation patterns, enabling site-specific discrimination of alanine residues within peptides or protein fragments. The combination of a removable Fmoc group and an unprotected acid functionality supports controlled deprotection, peptide bond formation, and downstream derivatization at the C-terminus.
1. Isotope-Labelled Peptide Synthesis
Fmoc-[15N]Ala-OH is applied in peptide synthesis where site-specific nitrogen labeling is required for quantitative NMR studies, kinetic monitoring, or fragment-based structural analysis. The Fmoc-protected nitrogen and free carboxylic acid allow incorporation into peptide chains using established coupling chemistries after Fmoc deprotection, while the [15N] label remains localized to the alanine residue. L-stereochemistry is retained through the building-block strategy, supporting stereochemically defined peptide analogs for structure determination and conformational studies. The resulting labeled peptides can serve as analytical standards or as defined probes for mapping backbone dynamics and residue-specific interactions in biochemical research.
2. Protein Engineering Studies
Fmoc-[15N]Ala-OH supports protein engineering workflows that rely on residue-level isotope discrimination to validate sequence incorporation, folding pathways, or interaction interfaces in engineered protein constructs. The amino acid derivative format, with Fmoc protection and a carboxylic acid handle, enables controlled assembly of labeled peptide segments that can be used in protein fragment studies, peptide-to-protein ligation strategies, or as mimetic components for binding assays. The [15N] signature can be tracked during spectroscopic characterization to confirm the presence and position of alanine residues within larger biomolecular assemblies. The approach aligns with amino acid chemistry strategies for chiral building block design and provides a chemically defined route to isotope-labeled intermediates for applied protein research.
3. Analytical NMR Standards
Fmoc-[15N]Ala-OH is utilized for analytical research requiring calibrated [15N] signals, including method development for 15N NMR, isotope ratio verification, and spectral assignment workflows. The isotopically enriched nitrogen is embedded in the alanine backbone, and the Fmoc carbamate can be removed to generate labeled alanine-containing fragments that simplify interpretation of nitrogen chemical shifts. The free carboxylic acid enables conversion to amide or ester derivatives when calibration compounds with defined functional groups are needed for instrument validation. The labeled residue structure supports reproducible mass-dependent behavior in MS-based confirmation of labeled peptide intermediates and final products.
4. Peptidomimetic Construction
Fmoc-[15N]Ala-OH is suitable for peptidomimetic and backbone-modified scaffold construction where labeled alanine units are incorporated to study structure-activity relationships or conformational preferences. The protected amine and carboxylic acid functionality facilitate sequential assembly into peptide-like chains, while the [15N] label can be retained through further functional group transformations that probe backbone recognition. Fmoc deprotection enables stepwise coupling, supporting stereochemically consistent incorporation of the L-alanine center into analogs used for receptor binding studies or mechanistic mapping. Downstream, labeled peptidomimetics can be used as defined chemical probes to correlate residue-level structural changes with physicochemical and binding properties in applied chemical biology.
5. Pharmaceutical Intermediate Preparation
Fmoc-[15N]Ala-OH can be employed as a labeled amino acid intermediate in pharmaceutical manufacturing-oriented fine chemical synthesis where isotopically defined reference materials are needed for process characterization and analytical method qualification. The Fmoc-protected amino group supports orthogonal protection logic, allowing controlled deprotection and coupling steps that align with peptide-building supply chains and validated synthetic routes. The free carboxylic acid enables conversion to activated derivatives for amide formation, supporting the preparation of labeled peptide intermediates used in impurity profiling, identity confirmation, or stability-related studies. The isotopic nitrogen label provides an additional analytical handle for distinguishing specific synthetic segments during downstream processing and characterization of peptide-containing materials.
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