Z-L-glutamic acid a-methyl ester
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Z-L-glutamic acid a-methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-003338
CAS number
5672-83-3
Molecular Formula
C14H17NO6
Molecular Weight
295.29
Z-L-glutamic acid a-methyl ester
IUPAC Name
(4S)-5-methoxy-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
Synonyms
Z-L-Glu-Ome; 1-Methyl N-Carbobenzoxy-L-Glutamate; N-Cbz-L-Glutamic Acid 1-Methyl Ester
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.272 g/cm3
Melting Point
64-72 °C
Boiling Point
510.6°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H17NO6/c1-20-13(18)11(7-8-12(16)17)15-14(19)21-9-10-5-3-2-4-6-10/h2-6,11H,7-9H2,1H3,(H,15,19)(H,16,17)/t11-/m0/s1
InChI Key
BGMCTGARFXPQML-NSHDSACASA-N
Canonical SMILES
COC(=O)C(CCC(=O)O)NC(=O)OCC1=CC=CC=C1

Z-L-glutamic acid a-methyl ester, a derivative of glutamic acid, boasts diverse applications in both research and industry. Here are four key applications:

Peptide Synthesis: Serving as a cornerstone in peptide synthesis, Z-L-glutamic acid a-methyl ester plays a crucial role in constructing peptide chains. Its esterified form simplifies coupling reactions necessary for crafting precise peptide sequences tailored for biochemical studies and pharmaceutical advancements. Researchers utilize this compound to design specific peptide structures with intricate functionality, enriching the landscape of biochemical exploration with its nuanced contributions.

Chiral Synthesis: Researchers leverage the unique stereochemistry of Z-L-glutamic acid a-methyl ester in synthesizing chiral molecules. Acting as a vital precursor or intermediate, it aids in establishing crucial chiral centers for pharmaceuticals and refined fine chemicals. By incorporating this compound, synthesized molecules acquire the desired optical activity, crucial for influencing their biological functions, enhancing the precision and efficacy of the synthesized compounds with a sophisticated touch of stereochemical finesse.

Enzyme Inhibition Studies: Delving into investigations exploring enzyme-inhibitor interactions, Z-L-glutamic acid a-methyl ester unveils insights into the intricate dynamics of enzymatic processes. Serving as a substrate mimic, this compound facilitates an in-depth exploration of how specific enzymes interact with inhibitors, laying the foundation for designing targeted enzyme-modulating drugs.

Taste Modulation Research: Stepping into the realm of food science, Z-L-glutamic acid a-methyl ester emerges as a focal point in unraveling taste modulation mysteries. Researchers probe into the compound's ability to shape flavor profiles, particularly enhancing the umami taste experience.

1.Characterization of the S'-subsite specificity of V8 proteinase via acyl transfer to added nucleophiles.
Schuster M1, Aaviksaar A, Schellenberger V, Jakubke HD. Biochim Biophys Acta. 1990 Dec 6;1036(3):245-7.
The S'-subsite specificity of endoproteinase Glu-C (V8 proteinase) was studied by acyl transfer reactions using Z-Glu-OMe as acyl donor and a series of amino acid- and peptide-derived nucleophiles. The partition constant, which characterizes specificity, was determined by a method based on the integrated rate equation. V8 proteinase prefers amino acid residues with hydrophobic side chains in the P'1 position. Di- and tripeptide amides are more efficient nucleophilic amino components than amino acid amides.
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