L-Propargylglycine
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L-Propargylglycine
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CAS No:
23235-01-0
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Formula:
C5H7NO2
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Chemical Name:
L-Propargylglycine
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Synonyms:
(S)-2-AMINO-4-PENTYNOIC ACID;RARECHEM BK PT 0255;(2R)-2-Aminopent-4-ynoic acid;H-GLY(PROPARGYL)-OH;H-PRA-OH;H-PRA-OH HCL;H-PROPARGYL-GLYCINE;H-PROPARGYL-GLY-OH
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CAS No:
Description
White powder
L-propargylglycine is a non-proteinogenic L-alpha-amino acid that is L-alanine in which one of the methyl hydrogens has been replaced by an ethynyl group.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.
Characteristics
63.3
-2.8
White to pale yellow Powder
1.2±0.1 g/cm3
232ºC
272°C at 760 mmHg
118.3±25.9 °C
1.513
2-8°C
0.00174mmHg at 25°C
Safety Information
NONH for all modes of transport
3
22-24/25
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
L-2-amino-4-pentynoic acid
L-Propargylglycine Use and Manufacturing
Intermediate 1; methyl (2S)-2-({[(1, 1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate To a solution of Step 1: (7S)-2-Chloro-7-(prop-2-yn-1-yl)-7, 8-dihydropteridin-6(5H)-one 2, 4-Dichloro-5-amino-pyrimidine (1 g, 6.1 mmol), The title compound was prepared using Click Chemistry 'Condition A?, which is a modification of a procedure previously described for this compound by Mindt.9 A solution of 1:1 tert-butanol/water (10 mL), commercially available
Computed Properties
Molecular Weight:113.11
XLogP3:-2.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:113.047678466
Monoisotopic Mass:113.047678466
Topological Polar Surface Area:63.3
Heavy Atom Count:8
Complexity:133
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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