L-Propargylglycine (CAS 23235-01-0)
See product citations (2)
QUICK LINKS
L-propargylglycine is an L-alpha-amino acid known for its unique chemical structure. It is derived from L-alanine, where one of the methyl hydrogens is substituted with an ethynyl group. This alteration leads to the irreversible inactivation of gamma-cystathionase (also called cystathionine gamma-lyase). Due to its properties, L-propargylglycine serves as an affinity labeling reagent for gamma-cystathionase and other enzymes. Moreover, L-propargylglycine acts as an inhibitor for various enzymes, including EC 1.4.3.2 (L-amino-acid oxidase), EC 2.6.1.2 (alanine transaminase), and EC 2.5.1.48 (cystathionine gamma-synthase). It exhibits characteristics of a non-proteinogenic L-alpha-amino acid and a terminal acetylenic compound. Notably, it exists as a tautomer of a L-propargylglycine zwitterion.
L-Propargylglycine (CAS 23235-01-0) References
- Effect of various alanine analogues on the L-alanine-adding enzyme from Escherichia coli. | Liger, D., et al. 1991. FEMS Microbiol Lett. 64: 111-5. PMID: 1855644
- Irreversible inactivation of snake venom l-amino acid oxidase by covalent modification during catalysis of l-propargylglycine. | Mitra, J. and Bhattacharyya, D. 2013. FEBS Open Bio. 3: 135-43. PMID: 23772385
- PHIP-label: parahydrogen-induced polarization in propargylglycine-containing synthetic oligopeptides. | Körner, M., et al. 2013. Chem Commun (Camb). 49: 7839-41. PMID: 23887355
- Effective PHIP labeling of bioactive peptides boosts the intensity of the NMR signal. | Sauer, G., et al. 2014. Angew Chem Int Ed Engl. 53: 12941-5. PMID: 25296746
- Hydrogen sulfide in posthemorrhagic shock mesenteric lymph drainage alleviates kidney injury in rats. | Han, B., et al. 2015. Braz J Med Biol Res. 48: 622-8. PMID: 25945746
- Sequence and Conformational Analysis of Peptide-Polymer Bioconjugates by Multidimensional Mass Spectrometry. | Sallam, S., et al. 2018. Biomacromolecules. 19: 1498-1507. PMID: 29554423
- Propargylglycine-based antimicrobial compounds are targets of TolC-dependent efflux systems in Escherichia coli. | Roldan, BJ., et al. 2020. Bioorg Med Chem Lett. 30: 126875. PMID: 31836438
- Cell-Free Biosynthesis of Lysine-Derived Unnatural Amino Acids with Chloro, Alkene, and Alkyne Groups. | Chen, Y., et al. 2023. ACS Synth Biol.. PMID: 37040607
- Suicide inactivation of bacterial cystathionine gamma-synthase and methionine gamma-lyase during processing of L-propargylglycine. | Johnston, M., et al. 1979. Biochemistry. 18: 4690-701. PMID: 387077
- Effect of L-propargylglycine on metabolism of sulfur-containing amino acids in pregnant rats and their fetuses. | Sasaki, K., et al. 1985. Biochem Int. 10: 165-75. PMID: 3994731
- Chloralanyl and propargylglycyl dipeptides. Suicide substrate containing antibacterials. | Cheung, KS., et al. 1983. J Med Chem. 26: 1733-41. PMID: 6417332
- Metabolic consequences of affinity labeling of cystathionase and alanine aminotransferase by L-propargylglycine in vivo. | Shinozuka, S., et al. 1982. Eur J Biochem. 124: 377-82. PMID: 7094918
- Irreversible inactivation of aspartate aminotransferases during transamination with L-propargylglycine. | Tanase, S. and Morino, Y. 1976. Biochem Biophys Res Commun. 68: 1301-8. PMID: 944577
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
L-Propargylglycine, 250 mg | sc-286102 | 250 mg | $68.00 | |||
L-Propargylglycine, 1 g | sc-286102A | 1 g | $100.00 | |||
L-Propargylglycine, 5 g | sc-286102B | 5 g | $370.00 | |||
L-Propargylglycine, 10 g | sc-286102C | 10 g | $630.00 | |||
L-Propargylglycine, 25 g | sc-286102D | 25 g | $1505.00 |