L-Propargylglycine
- Product Name
- 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
- Formula Weight
- 113.11
- MOL File
- 23235-01-0.mol
L-Propargylglycine Property
- Boiling point:
- 272.1±35.0 °C(Predicted)
- Density
- 1.209±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,2-8°C
- form
- Powder
- pka
- 2.04±0.10(Predicted)
- color
- White to pale yellow
- BRN
- 2347861
- InChIKey
- DGYHPLMPMRKMPD-BYPYZUCNSA-N
- CAS DataBase Reference
- 23235-01-0(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- 81838
- Product name
- L-C-Propargylglycine
- Purity
- ≥99.0% (TLC)
- Packaging
- 250mg
- Price
- $1030
- Updated
- 2024/03/01
- Product number
- 287589
- Product name
- L-Propargylglycine
- Packaging
- 250mg
- Price
- $350
- Updated
- 2021/12/16
- Product number
- A629368
- Product name
- (S)-2-Aminopent-4-ynoicAcid
- Packaging
- 100mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- AS39979
- Product name
- (S)-2-Aminopent-4-ynoic acid
- Purity
- 97% ee
- Packaging
- 1g
- Price
- $86
- Updated
- 2021/12/16
- Product number
- 02726
- Product name
- L-Propargylglycine
- Packaging
- 1G
- Price
- $50.4
- Updated
- 2021/12/16
L-Propargylglycine Chemical Properties,Usage,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L-propargylglycine is a non-proteinogenic L-alpha-amino acid that is L-alanine in which one of the methyl hydrogens has been replaced by an ethynyl group.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
Raw materials
Preparation Products
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View Lastest Price from L-Propargylglycine manufacturers
- Product
- L-Propargylglycine 23235-01-0
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1T+
- Release date
- 2024-04-12