Description

(S)-2-Amino-2-methylpent-4-ynoic acid (CAS: 1231709-27-5) is a high-purity chiral amino acid derivative with the molecular formula C₆H₉NO₂. This compound, also known as (S)-α-Propargylalanine, features a propargyl group and a methyl substitution at the α-carbon, making it a valuable building block for peptide synthesis and medicinal chemistry applications. With a guaranteed purity of ≥98% (HPLC) and high enantiomeric excess (>98% ee), this product is ideal for researchers requiring precise stereochemical control in drug discovery, bioconjugation, and enzyme inhibition studies. The compound is supplied as a white to off-white crystalline powder, soluble in water and organic solvents like DMSO or methanol, ensuring versatility in experimental workflows. Store at 2-8°C under inert conditions to maintain stability.

Properties

• CAS Number: 1231709-27-5
• Complexity: 167
• IUPAC Name: (2S)-2-amino-2-methyl-pent-4-ynoic acid
• InChI: InChI=1S/C6H9NO2/c1-3-4-6(2,7)5(8)9/h1H,4,7H2,2H3,(H,8,9)/t6-/m0/s1
• InChI Key: FSBNDYYRTZBHAN-LURJTMIESA-N
• Exact Mass: 127.063328530
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14
• SMILES: C[C@](CC#C)(C(=O)O)N
• Topological: 63.3
• Monoisotopic Mass: 127.063328530
• Synonyms: 1231709-27-5, (S)-2-Amino-2-methylpent-4-ynoic acid, (2S)-2-AMINO-2-METHYLPENT-4-YNOIC ACID, alpha-Me-Gly(Propargyl)-OH, H-alpha-Prg-D-Ala-OH, alpha-methyl-D-Propargylglycine, 4-Pentynoic acid, 2-amino-2-methyl-, (2S)-, MFCD10567140, (S)-2-Amino-2-methylpent-4-ynoicacid, SCHEMBL602183, DTXSID40679815, AKOS016844154, AT32904, DA-59344, HY-151664, CS-0617890, (S)-(-)-alpha-Propargylalanine, >=98.0% (HPLC), S-1231709-27-5, (S)-a-Propargylalanine, (S)-2-Amino-2-methyl-4-pentynoic acid (>98%, >98%ee) (H-L-aMePra-OH)

(S)-2-Amino-2-methylpent-4-ynoic acid is widely used in peptide modification and click chemistry due to its alkyne-functionalized side chain. It serves as a key intermediate for synthesizing constrained peptides and bioactive molecules targeting neurological disorders. Researchers also employ it as a chiral auxiliary in asymmetric catalysis or as a metabolic probe in biochemical studies. Its rigid structure enhances binding affinity in enzyme inhibitor design, particularly for proteases and transaminases.

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