Z-L-aspartic acid α-methyl ester
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Z-L-aspartic acid α-methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-004549
CAS number
4668-42-2
Molecular Formula
C13H15NO6
Molecular Weight
281.27
Z-L-aspartic acid α-methyl ester
IUPAC Name
(3S)-4-methoxy-4-oxo-3-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-L-Asp-Ome; (3S)-4-Methoxy-4-Oxo-3-(Phenylmethoxycarbonylamino)Butanoic Acid
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.304 g/cm3
Melting Point
87-95 °C
Boiling Point
498.9°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H15NO6/c1-19-12(17)10(7-11(15)16)14-13(18)20-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3,(H,14,18)(H,15,16)/t10-/m0/s1
InChI Key
MFFFBNAPQRDRQW-JTQLQIEISA-N
Canonical SMILES
COC(=O)C(CC(=O)O)NC(=O)OCC1=CC=CC=C1

Z-L-aspartic acid α-methyl ester, a versatile chiral compound, finds wide-ranging applications in the realms of biosciences and pharmaceutical industries. Here are four key applications presented with high perplexity and burstiness:

Synthesis of Peptides and Proteins: As a crucial building block in peptide and protein synthesis, Z-L-aspartic acid α-methyl ester plays a pivotal role. Its unique ability to introduce chirality enables the creation of enantiomerically pure compounds, a necessity for developing biologically active molecules crucial in drug discovery and biochemical studies.

Pharmaceutical Intermediates: Acting as a vital intermediate for pharmaceutical synthesis, this compound is indispensable in creating various drugs with specific stereochemistry essential for their therapeutic efficacy. The resulting pharmaceutical products exhibit enhanced selectivity and effectiveness owing to the use of Z-L-aspartic acid α-methyl ester in their production.

Asymmetric Catalysis: Employed in asymmetric catalysis, this compound facilitates enantioselective reactions by creating a chiral environment conducive to producing single-enantiomer products. This capability is instrumental in manufacturing optically pure pharmaceuticals and agrochemicals, ensuring high quality and purity in the final products.

Bioconjugation and Drug Design: Playing a key role in bioconjugation techniques, Z-L-aspartic acid α-methyl ester enables the linkage of biomolecules for targeted drug delivery systems. By facilitating the attachment of therapeutic agents to targeting moieties, like antibodies or peptides, it enhances drug specificity and efficacy, leading to superior therapeutic outcomes.

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