Fmoc-[15N]Gly-OH is an Fmoc-protected, isotopically labeled glycine derivative in which the amino nitrogen bears the 15N isotope, and the backbone retains the characteristic amino acid framework. The molecule contains an Fmoc carbamate protecting group on the amino functionality and a free carboxylic acid (-COOH), with the side chain reduced to a single hydrogen typical of glycine while the labeled nitrogen provides an isotopic signature for mass-based detection. In synthesis and analytical workflows, it functions as a protected amino acid building block for stepwise peptide assembly and as an isotopic tracer for NMR/MS method development, labeling studies, and quantitative tracking of glycine incorporation at the nitrogen position.
CAT No: CP26270
CAS No:125700-33-6
Synonyms/Alias:Fmoc-Gly-OH-15N;Glycine-15N,N-Fmoc;N-(9-Fluorenylmethoxycarbonyl)-glycine-15N;125700-33-6;485756_ALDRICH;N-(9-fluorenylmethoxycarbonyl)glycine-15N
Fmoc-[15N]Gly-OH is an Fmoc-protected glycine labeled at the backbone nitrogen with the stable isotope 15N, providing a defined chiral-neutral amino acid building block for peptide and protein chemistry. The structure combines the glycine α-amino acid motif with an Fmoc carbamate protecting group on nitrogen and a free carboxylic acid for controlled coupling chemistry. Isotopic substitution at the amide-forming nitrogen enables unambiguous mass shifts in LC-MS and NMR-based readouts, while the Fmoc group supports standard solid-phase or solution-phase peptide assembly workflows. The compound's functional group pattern, including the protected amine and the acid handle, makes it suitable for incorporation into peptides and for downstream synthetic transformations that preserve the labeled backbone nitrogen.
1. Isotope-Labeled Peptide Synthesis
Fmoc-[15N]Gly-OH supports isotope-resolved peptide construction in chemical biology and analytical peptide workflows by pairing an Fmoc-protected amine with a carboxylic acid for amide bond formation. The 15N label resides on the glycine backbone nitrogen that becomes part of the peptide linkage upon coupling, enabling direct tracking of incorporation sites and monitoring of fragmentation patterns in tandem mass spectrometry. Fmoc deprotection strategies allow stepwise assembly while maintaining isotopic integrity through subsequent coupling and purification steps. Labeled glycine residues generated from this building block can serve as internal standards or mechanistic probes in studies of peptide stability, proteolysis, and sequence-dependent conformational behavior.
2. Protein Engineering Tracing
Fmoc-[15N]Gly-OH is applicable to protein engineering and protein chemistry where site-specific backbone nitrogen labeling is used to interrogate structure and dynamics. The glycine residue's small side chain minimizes steric perturbation, while the labeled nitrogen provides a spectroscopic handle for NMR experiments that distinguish labeled amide environments from unlabeled residues. Fmoc protection enables controlled incorporation into peptide segments that can be assembled into larger constructs, including labeled fragments used in recombinant or semisynthetic protein workflows. The resulting 15N-containing peptides can be employed to map conformational changes, quantify local exchange processes, or validate computational models of backbone motion.
3. LCMS Quantitation Standards
Fmoc-[15N]Gly-OH can be used to prepare isotope-tagged peptide standards for analytical research and method development in proteomics and metabolomics. The Fmoc-protected amino acid format supports synthesis of defined labeled peptides, and the 15N label yields predictable mass offsets that improve selectivity in targeted LC-MS/MS quantitation. The free carboxyl functionality enables incorporation into peptide sequences that mimic analyte termini or internal motifs, improving calibration accuracy for digestion-based workflows. Isotopically defined glycine-containing peptide standards derived from this compound can be applied to assay validation, impurity profiling, and confirmatory identification in complex matrices.
4. Peptidomimetic Building Blocks
Fmoc-[15N]Gly-OH functions as a chiral-neutral amino acid intermediate for peptidomimetic construction where backbone amide nitrogen labeling is retained in analogs. The Fmoc group provides a removable protecting strategy compatible with peptide coupling chemistry, while the glycine core can be used as a minimal spacer in constrained scaffold designs. 15N incorporation into the amide linkage can support mechanistic studies of receptor binding or enzyme recognition when analogs are analyzed by isotope-sensitive spectroscopic methods. Downstream transformations that convert the carboxyl group into activated derivatives can enable assembly of labeled peptidomimetics used in structure-activity relationship studies and chemical probe development.
5. Process Chemistry Intermediate
Fmoc-[15N]Gly-OH is suitable for process chemistry intermediate preparation where isotope-labeled amino acid derivatives are manufactured with consistent labeling for downstream synthesis. The Fmoc-protected amine and carboxylic acid functionality align with established protection/deprotection and coupling paradigms used in peptide manufacturing supply chains. The stable isotope label at nitrogen is chemically robust under typical peptide synthesis conditions, supporting reproducible incorporation into final labeled products. Industrially relevant handling of this intermediate can include preparation of labeled peptide building blocks and calibration reagents used for quality control in isotope-based analytical workflows.
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