L-Propargylglycine
- CAS No.
- 23235-01-0
- Chemical Name:
- L-Propargylglycine
- Synonyms
- H-PRA-OH;L-Pra-OH;H-L-Pra-OH;H-PRA-OH HCL;L-Proparglycine;L-PROPARGYL-GLY-OH;L-PROPARGYLGLYCINE;H-PROPARGYL-GLY-OH;H-GLY(PROPARGYL)-OH;RARECHEM BK PT 0255
- CBNumber:
- CB6208192
- Molecular Formula:
- C5H7NO2
- Molecular Weight:
- 113.11
- MDL Number:
- MFCD00077855
- MOL File:
- 23235-01-0.mol
| Boiling point | 272.1±35.0 °C(Predicted) |
|---|---|
| Density | 1.209±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,2-8°C |
| pka | 2.04±0.10(Predicted) |
| form | Powder |
| color | White to pale yellow |
| BRN | 2347861 |
| InChIKey | DGYHPLMPMRKMPD-BYPYZUCNSA-N |
| CAS DataBase Reference | 23235-01-0(CAS DataBase Reference) |
| FDA UNII | 8R9U8RVT6V |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319-H335 |
| Precautionary statements | P280-P261 |
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
| F | 10 |
| HS Code | 29224999 |
L-Propargylglycine price More Price(35)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 81838 | L-C-Propargylglycine ≥99.0% (TLC) | 23235-01-0 | 250mg | $1030 | 2024-03-01 | Buy |
| Usbiological | 287589 | L-Propargylglycine | 23235-01-0 | 250mg | $350 | 2021-12-16 | Buy |
| TRC | A629368 | (S)-2-Aminopent-4-ynoicAcid | 23235-01-0 | 100mg | $60 | 2021-12-16 | Buy |
| Activate Scientific | AS39979 | (S)-2-Aminopent-4-ynoic acid 97% ee | 23235-01-0 | 1g | $86 | 2021-12-16 | Buy |
| Chem-Impex | 02726 | L-Propargylglycine | 23235-01-0 | 1G | $50.4 | 2021-12-16 | Buy |
L-Propargylglycine Chemical Properties,Uses,Production
Chemical Properties
White powder
Definition
ChEBI: L-propargylglycine is a non-proteinogenic L-alpha-amino acid that is L-alanine in which one of the methyl hydrogens has been replaced by an ethynyl group. It causes the irreversible inactivation of gamma-cystathionase (also known as cystathionine gamma-lyase) and is used as an affinity labeling reagent for gamma-cystathionase and other enzymes. It has a role as an EC 1.4.3.2 (L-amino-acid oxidase) inhibitor, an EC 2.6.1.2 (alanine transaminase) inhibitor and an EC 2.5.1.48 (cystathionine gamma-synthase) inhibitor. It is a non-proteinogenic L-alpha-amino acid and a terminal acetylenic compound. It is a tautomer of a L-propargylglycine zwitterion.
Enzyme inhibitor
This alkynyl amino acid and mechanism-based inhibitor (FW = 113.11 g/mol; CAS 23235-01-0), also known as (S)-2-amino-4-pentynoic acid, irreversibly inactivates γ-cystathionase (an enzyme that also catalyzes the synthesis of the metabolic signaling gas, H2S, See also Hydrogen Sulfide), acting as a Michael addition type suicide inhibitor of cystathionine γ-lyase, cystathionine γ-synthase, alanine aminotransferase, and methionine γ-lyase. Propargylglycine inactivates γ-cystathionase with pseudo-first-order kinetics and incorporation of 1 mol inhibitor per 80 kDa enzyme. When studied in vivo, inactivation of cystathionine γ-lyase in rat kidney was less than that in the liver, owing to the presence of a higher cysteine concentration in kidney. L-Propargylglycine was found to inactivate pig heart L-alanine transaminase (EC 2.6.1.2) at 37o C with a Ki = 3.9 mM, an observed maximal first order rate constant, kinact = 0.26 min–1, a minimal stoichiometric ratio necessary for inactivation of 2.7 L-propargylglycine molecules/enzyme subunit, with 2.2 molecules/subunit undergoing transamination before inactivation ensues. Experimental cystathioninuria, induced in rats by administration of D,L-propargylglycine, results in the formation of the cystathionine metabolites, cystathionine ketimine and perhydro-1,4-thiazepine-3,5-dicarboxylic acid, in various regions of the brain. L-Propargylglycine irreversibly inactivates proline dehydrogenase, which catalyzes the first step of proline catabolism, oxidizing proline to pyrroline-5-carboxylate. The 1.9-? resolution structure of the inactivated Thermus thermophilus enzyme shows that N5 of the flavin cofactor is covalently connected to the e-amino group of Lys-99 via a three-carbon linkage, consistent with the mass spectral analysis of the inactivated enzyme. The isoalloxazine ring has a butterfly angle of 25o, suggesting the cofactor is reduced. Two mechanisms, both involving oxidation to N-propargyliminoglycine, can account for these properties. L-Propargylglycine irreversibly inhibits L-amino acid oxidase from the venom of Crotalus adamanteus (Eastern diamondback rattlesnake) and Crotalus atrox (Western diamondback rattlesnake) in a dose- and timedependent manner that was blocked by the substrate L-phenylalanine. Other targets include methionineγ-lyase and UDP-Nacetylmuramate: L-alanine ligase, or L-alanine-adding enzyme, or UDP-Nacetylmuramoyl- L-alanine synthetase.
Purification Methods
The acid crystallises readily when ~4g in 50mL H2O are treated with absolute EtOH at 4o/3hours, and is collected, washed with cold absolute EtOH and Et2O and dried in a vacuum. Also, it recrystallises from aqueous Me2CO, RF on SiO2 TLC plates with n-BuOH/H2O/AcOH (4:1:1) is 0.26. The racemate has m 238-240o. [Leukart et al. Helv Chim Acta 59 2181 1976, Eberle & Zeller Helv Chim Acta 68 1880 1985, Jansen et al. Recl Trav Chim Pays-Bas 88 819 1969.] It is a suicide inhibitor of -cystathionase and other enzymes [Washtier & Abeles Biochemistry 16 2485 1977, Shinozuka et al. Eur J Biochem 124 377 1982].
L-Propargylglycine Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Sichuan HongRi Pharma-Tech Co.,Ltd | +86-028-64841719 +8618980456393 | daisy@enlaibio.com | China | 1369 | 58 |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29797 | 60 |
| Nanjing ChemLin Chemical Industry Co., Ltd. | 025-83697070 | product@chemlin.com.cn | CHINA | 3012 | 60 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| GenicBio Limited | +86-21-37621270 | service@genicbio.com | CHINA | 991 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28180 | 58 |
| Chongqing Chemdad Co., Ltd | +86-023-61398051 +8613650506873 | sales@chemdad.com | China | 39916 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49390 | 58 |
| Fuxin Pharmaceutical | +86-021-021-50872116 +8613122107989 | contact@fuxinpharm.com | China | 10297 | 58 |
| Guangzhou Yuheng Pharmaceutical Technology Co., Ltd | +8613580539051 | joe@yuhengpharm.com | CHINA | 21149 | 58 |
View Lastest Price from L-Propargylglycine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-28 | L-Propargylglycine
23235-01-0
|
US $0.00-0.00 / kg | 1kg | 98% | 1T+ | Sichuan HongRi Pharma-Tech Co.,Ltd | |
 |
2023-03-16 | L-Propargylglycine
23235-01-0
|
US $14.00 / kg | 1kg | 99% | 5000 tons | Hebei Duling International Trade Co. LTD |
-
- L-Propargylglycine
23235-01-0
- US $0.00-0.00 / kg
- 98%
- Sichuan HongRi Pharma-Tech Co.,Ltd
-
- L-Propargylglycine
23235-01-0
- US $14.00 / kg
- 99%
- Hebei Duling International Trade Co. LTD