Propargylglycine, DL- is an alkyne-containing amino acid enabling click-chemistry conjugation and structural modification. The triple bond offers bioorthogonal reactivity and rigid geometry. Researchers use it to design labeled peptides and conformational probes. Its versatile backbone suits synthetic diversification.
CAT No: R2137
CAS No:50428-03-0
Synonyms/Alias:DL-Propargylglycine;2-Aminopent-4-ynoic acid;50428-03-0;64165-64-6;2-Amino-4-pentynoic acid;D,L-Propargylglycine;H-DL-Pra-OH;DL-PROPARGYL-GLY-OH;DL-2-Propynylglycine;(R)-alpha-Propargylglycine;2-propargylglycine;FU67PLJ48R;MFCD00056728;NSC-21940;PROPARGYLGLYCINE, DL-;H-Propargyl-DL-Gly-OH;(RS)-2-Amino-4-pentynoic acid;Propargylglycine (R,S);Propargyl glycine;h-propargyl-d-glycine;2-Propynylglycine;UNII-FU67PLJ48R;DTXSID60941728;4-Pentynoic acid, 2-amino-;(+-)-2-Amino-4-pentynoic acid;NSC 21940;4-Pentynoic acid, 2-amino-, (+-)-;H-Propargyl-DL-Gly-OH;2-Aminopent-4-ynoicacid;2-azaniumylpent-4-ynoate;2-azanylpent-4-ynoic acid;2-Amino-pent-4-ynoic acid;SCHEMBL40887;DL-Propargylglycine;(+/-)-2-Amino-4-pentynoic acid;CHEMBL4795578;BDBM367671;DTXCID401370153;DTXSID301033465;BCP11742;NSC21940;AKOS000195110;AKOS022185126;AB88461;AB89124;AC-9946;CS-W020864;FP49054;HY-W040124;s10337;AS-18031;DA-52607;SY139497;2-amino-4-pentynoic acid, monohydrochloride;EN300-108370;4-PENTYNOIC ACID, 2-AMINO-, (+/-)-;A835369;US10227314, Compound 2-aminopent-4-ynoic acid;Q27278205;DL-Propargylglycine, cystathionine gamma-lyase inhibitor;F8881-1986;DL-Propargyl-Gly-OH;DL-Pra-OH;2-Amino-4-pentynoic acid;628-118-3;827-880-6;
Propargylglycine, DL- is a synthetic, non-proteinogenic amino acid featuring a propargyl group attached to the α-carbon of glycine. As a structurally unique analog within the amino acid family, it is well recognized for its role as an irreversible inhibitor of certain pyridoxal phosphate-dependent enzymes, particularly cystathionine γ-lyase. Its distinctive chemical structure enables researchers to probe sulfur amino acid metabolism, enzyme mechanisms, and structure-activity relationships within a variety of biochemical and molecular biology settings. The compound's dual enantiomeric form (DL-) broadens its utility for studies that do not require stereospecificity, making it a versatile tool in fundamental research and specialized biochemical applications.
Enzyme inhibition studies: Propargylglycine is extensively utilized as a mechanism-based inhibitor in investigations of cystathionine γ-lyase and related pyridoxal phosphate-dependent enzymes. By covalently modifying the active site, it enables researchers to dissect enzyme catalytic mechanisms and elucidate the functional roles of target enzymes in sulfur-containing amino acid pathways. Its use in these studies provides critical insights into enzyme specificity, reaction intermediates, and the regulation of metabolic flux through the transsulfuration pathway.
Metabolic pathway elucidation: In metabolic research, this compound serves as a valuable probe for mapping the biosynthesis and catabolism of sulfur amino acids such as cysteine and homocysteine. Inhibition of key enzymes using propargylglycine allows for the controlled perturbation of metabolic networks, facilitating the identification of pathway intermediates, regulatory nodes, and compensatory mechanisms. Such studies are essential for expanding the understanding of amino acid homeostasis and the broader implications of sulfur metabolism in cellular physiology.
Analytical biochemistry: The distinct chemical reactivity of propargylglycine supports its application in analytical assays designed to quantify enzyme activity, substrate specificity, and the effects of inhibitors on biochemical reactions. Its use as a reference inhibitor or mechanistic probe in spectrophotometric, chromatographic, or mass spectrometric assays enables precise characterization of enzyme kinetics and inhibitor potency, supporting both fundamental enzymology and applied biochemical screening efforts.
Protein engineering and mechanistic studies: Due to its ability to form covalent adducts with enzyme active sites, propargylglycine is a useful tool in protein engineering and mechanistic biochemistry. Researchers employ it to induce site-specific modifications, stabilize reaction intermediates, or trap transient enzyme-substrate complexes for structural and functional analysis. These applications advance the understanding of enzyme architecture, catalytic residues, and the molecular basis of substrate recognition.
Cellular metabolism research: In cell-based studies, propargylglycine is used to modulate intracellular sulfur amino acid pools and investigate the downstream effects of altered transsulfuration pathway activity. By selectively inhibiting cystathionine γ-lyase in cultured cells or tissue extracts, scientists can assess the impact on cellular redox balance, glutathione synthesis, and the integration of sulfur metabolism with other metabolic networks. Such experiments are instrumental in revealing the interplay between amino acid metabolism and cellular physiology under various experimental conditions.
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