Z-L-aspartic acid α-benzyl ester
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Z-L-aspartic acid α-benzyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-004548
CAS number
4779-31-1
Molecular Formula
C19H19NO6
Molecular Weight
357.40
Z-L-aspartic acid α-benzyl ester
IUPAC Name
(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-L-Asp-Obzl; 1-Benzyl N-carbobenzyloxy-L-aspartate; N-Carbobenzyloxy-L-aspartic acid 1-benzyl Ester
Appearance
White to off-white powder
Purity
98-101% (Assay by titration)
Density
1.293 g/cm3
Melting Point
83-85 °C
Boiling Point
583.5°C
Storage
Store at RT
InChI
InChI=1S/C19H19NO6/c21-17(22)11-16(18(23)25-12-14-7-3-1-4-8-14)20-19(24)26-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,24)(H,21,22)/t16-/m0/s1
InChI Key
UYOZWZKJQRBZRH-INIZCTEOSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)C(CC(=O)O)NC(=O)OCC2=CC=CC=C2

Z-L-aspartic acid α-benzyl ester, a versatile chemical compound, finds applications across research and pharmaceutical industries. Explore its diverse uses presented with high perplexity and burstiness.

Peptide Synthesis: Serving as a foundational element in peptide synthesis, Z-L-aspartic acid α-benzyl ester acts as a crucial building block. It plays a dual role by safeguarding the aspartic acid residue, thus facilitating seamless peptide bond formation, while shielding the α-carboxyl group from unwanted side reactions. Researchers leverage this compound to craft intricate peptides for applications in drug discovery and protein engineering, unlocking realms of possibilities in synthetic chemistry.

Enzyme Inhibitor Development: Delving into medicinal chemistry, Z-L-aspartic acid α-benzyl ester emerges as a pivotal precursor for tailoring specific inhibitors targeting aspartic proteases. These enzymatic warriors play pivotal roles in various afflictions, such as HIV and cancer. By harnessing the core structure of this compound, scientists engineer inhibitors with precision, paving the path for potential therapeutic candidates aimed at combating these proteases and thwarting disease progression.

Chiral Derivative Production: Embracing the realm of asymmetric synthesis in organic chemistry, Z-L-aspartic acid α-benzyl ester stands tall in the creation of chiral derivatives. Its shielded scaffold enables selective reactions essential for generating enantiomerically pure compounds, pivotal in therapeutic regimens. These derivatives serve as linchpins in pharmaceutical and fine chemical synthesis, offering enhanced efficacy and minimized side effects in drug development.

Biochemical Research: Unleashing its potential in biochemical inquiries, Z-L-aspartic acid α-benzyl ester becomes a beacon for unraveling protein-ligand interactions and structure-activity relationships. This compound integrates seamlessly into peptides or small molecules, offering insights into binding affinities and biological activities. Such investigations shed light on the intricate molecular dance of enzyme function and aid in sculpting novel bioactive compounds.

1.Potent GnRH agonists containing L-amino acid derivatives in the six position.
Seprödi J, Erchegyi J, Vadász Z, Teplán I, Mezö I, Kanyicska B, Kovács M, Vigh S. Biochem Biophys Res Commun. 1987 May 14;144(3):1214-21.
New agonists related to gonadotropin-releasing hormone (GnRH) have been synthesized that are comparable in potency to the GnRH and its superagonists for release of LH and estrus suppression without substitutions with D- or unnatural amino acids in position 6. We now report a series of L-beta-aspartyl-6 GnRH analogs containing only naturally occurring L-amino acids in the whole sequence, exhibiting considerable in vivo biological activity. Dose and time dependent LH release capability of the different analogs in adult male mice, estrus suppression comparisons and blockade of ovulation in female rats are given. The incorporation of L-Asp-OMe and L-Asp-OBzl in position 6 of GnRH resulted in the most potent GnRH agonists (to 12-20xGnRH potency) in this series inducing a biphasic biological response similar to the D-amino acid-6 substituted superactive GnRH analogs. A correlation between the LH releasing potencies of the analogs and their HPLC retention times was also investigated.
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