(S)-2-allyl-Gly, CAS No. 16338-48-0

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16338-48-0

Catalog No. EBD2207882

CAS 16338-48-0

Name (S)-2-allyl-Gly

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Basic Information

Synonyms: L-2-aminopent-4-enoicacid (S)-2-allyl-Gly (S)-(-)-2-Amino-4-pentenoicacid (S)-2-Amino-4-PentenoicAcid RARECHEMBKPT0249 3-Vinyl-L-Alanine L-C-Allylglycine L-Alpha-Allyl-Gly L-Alpha-Allyl-Glycine H-(Allyl)Gly-Oh (2S)-2-Aminopent-4-EnoicAcid H-Gly(Allyl)-Oh l-alpha-allylglycine

Molecular Formula: C5H9NO2

Molecular Weight: 115.13

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

(S)-2-Allylglycine, also known as (S)-(-)-2-amino-4-pentenoic acid, is a non-proteinogenic, unsaturated amino acid derivative. It features an allyl side chain attached to the alpha-carbon of the glycine backbone in the (S)-configuration. This structure makes it a valuable chiral building block and a functional analog of natural amino acids. This compound is primarily recognized in biochemical and pharmacological research. It acts as a potent and irreversible inhibitor of glutamate decarboxylase (GAD), a key enzyme in the biosynthesis of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA). Due to this mechanism, (S)-2-allylglycine is extensively used as a research tool to induce GABA deficiency in experimental models, facilitating the study of epilepsy, seizures, and other neurological disorders linked to GABAergic system dysfunction. Beyond its role as a biochemical probe, its chiral amine and carboxylic acid functionalities make it a versatile intermediate in organic synthesis, particularly for constructing more complex peptide mimetics and pharmacologically active molecules. It requires careful handling as it may cause skin and eye irritation.

Physical Properties

Color: white

Melting Point: 283 °C (dec.)(lit.)

Boiling Point: 231 °C at 760 mmHg

Flash Point: 93.5 °C

Density: 1.098 g/cm3

Solubility: H2O: 100 mg/mL

Storage: room temp

Analytical Data

Appearance: White to off-white crystalline powder