ChemicalBook > CAS DataBase List > L-Propargylglycine

L-Propargylglycine

Product Name: L-Propargylglycine
CAS No.: 23235-01-0
Chemical Name: L-Propargylglycine
Synonyms: L-PRG;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
CBNumber: CB6208192
Molecular Formula: C5H7NO2
Formula Weight: 113.11
MOL File: 23235-01-0.mol

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L-Propargylglycine Property

Melting point:: 235-239°C
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
InChI: InChI=1S/C5H7NO2/c1-2-3-4(6)5(7)8/h1,4H,3,6H2,(H,7,8)/t4-/m0/s1
InChIKey: DGYHPLMPMRKMPD-BYPYZUCNSA-N
SMILES: C(O)(=O)[C@@H](N)CC#C
CAS DataBase Reference: 23235-01-0(CAS DataBase Reference)

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
F: 10
HS Code: 29224999

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 81838
Product name: L-C-Propargylglycine
Purity: ≥99.0% (TLC)
Packaging: 250mg
Price: $1060
Updated: 2025/07/31

TRC

Product number: A629368
Product name: (S)-2-Aminopent-4-ynoicAcid
Packaging: 100mg
Price: $60
Updated: 2021/12/16

Usbiological

Product number: 287589
Product name: L-Propargylglycine
Packaging: 250mg
Price: $350
Updated: 2021/12/16

AK Scientific

Product number: M624
Product name: L-Propargylglycine
Packaging: 250mg
Price: $32
Updated: 2021/12/16

Chem-Impex

Product number: 02726
Product name: L-Propargylglycine
Packaging: 250MG
Price: $33.6
Updated: 2021/12/16

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L-Propargylglycine Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

Reagent for the irreversible inactivation of γ-cystathionase; affinity labeling reagent for γ-cystathionase and other enzymes; peptides containing this amino acid can be tritiated to high specific radioactivity

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.

Biological Activity

L-C-Propargylglycine, a specific inhibitor of H(2)S synthase of cystathionine-γ-lyase (CSE), may be used to study the role of H2S in regulation of biological processes.', 'L-propargylglycine (PAG), an inhibitor of cystathionine γ-lyase (CSE), is useful in studies of hydrogen sulphide synthesis and bioactivity.

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

Sichuan HongRi Pharma-Tech Co.,Ltd

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

23235-01-0, L-PropargylglycineRelated Search:

4-Aminophenylacetic acid 4-Hydroxy-D-(-)-2-phenylglycine 3-Chloropropyne Glycine Propargyl bromide FMOC-D-PROPARGYLGLYCINE FMOC-L-PROPARGYLGLYCINE (R)-N-BOC-Propargylglycine DL-PROPARGYLGLYCINE (S)-N-BOC-Propargylglycine (R)-2-aminopent-4-ynoic acid L-Propargylglycine HCL DL-PROPARGYL-GLY-OH 4-PENTYNOIC ACID BOC-L-PROPARGYLGLYCINE DCHA SALT propargylglycin H-GLY-PRO-PNA HCL (S)-PROPARGYLGLYCINE METHYL ESTER HYDROCHLORIDE,L-PROPARGYLGLYCINE METHYL ESTER HYDROCHLORIDE

(2R)-2-Aminopent-4-ynoic acid

(S)-2-AMINO-4-PENTYNOIC ACID

RARECHEM BK PT 0255

H-GLY(PROPARGYL)-OH

H-PRA-OH

H-PRA-OH HCL

H-PROPARGYL-GLYCINE

H-PROPARGYL-GLY-OH

L-C-PROPARGYLGLYCINE

L-PROPARGYLGLYCINE

L-PROPARGYL-GLY-OH

4-Pentynoic acid, 2-amino-, (2S)-

H-pra-OH hydrochloride

(S)-alpha-Propargylglycine, 98% ee, 98%

(S)-2-AMinopent-4-ynoic acid

H-Propargyl-Gly-OH, (S)-2-AMino-4-pentynoic acid

(S)-alpha-Propargylglycine, 98%, 98% ee

(S)-2-Propargylglycine

(2S)-2-Aminopent-4-ynoic acid, 2-(Prop-2-yn-1-yl)-L-glycine

2-Propargyl-L-glycine

(S)-alpha-Propargylglycine

L-Proparglycine

L-Pra-OH

L-Propargylglycine≥ 99% (HPLC, Chiral purity)

(S)-α-Propargylglycine, 98% ee

(2S)-2-Amino-4-pentynoic acid

2-(2-Propynyl)-L-glycine

H-L-Pra-OH

L-Propargylglycine, >=98%

L-C-Propargylglycine >=99.0% (TLC)

L-Propargylglycine USP/EP/BP

(2S)-2-azaniumylpent-4-ynoate

(S)-α-Propargylglycine

L-Propargylglycine,97%

(S)-a-Propargylglycine

<sc>L</sc>-C-Propargylglycine

L-PRG

23235-01-0

C5H7NO2HCl

Glycine Derivatives

Specialty Synthesis

Peptide Synthesis

Unnatural Amino Acid Derivatives

Antibiotics

Unusual amino acids

Amino Acids