Aspartic acid, N-[(phenylmethoxy)carbonyl]-, 4-methyl ester
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Aspartic acid, N-[(phenylmethoxy)carbonyl]-, 4-methyl ester

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4-methyl ester of N-[(phenylmethoxy)carbonyl]-aspartic acid, a compound of interest in the biomedical sector due to its purported efficacy in addressing neural maladies or neurotransmitter-related ailments.

Category
CBZ-Amino Acids
Catalog number
BAT-008018
CAS number
3160-47-2
Molecular Formula
C13H15NO6
Molecular Weight
281.26
Aspartic acid, N-[(phenylmethoxy)carbonyl]-, 4-methyl ester
IUPAC Name
(2S)-4-methoxy-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-Asp(OMe)-OH; (S)-2-N-Cbz-Amino-Succinic Acid 4-Methyl Ester; Cbz-L-Aspartic Acid 4-Methyl Ester; N-Benzyloxycarbonyl-L-Aspartic Acid 4-Methyl Ester
Appearance
White powder
Purity
≥ 98%
Density
1.304 g/cm3
Boiling Point
503.6°C at 760 mmHg
Storage
Store at 2-8°C
InChI
InChI=1S/C13H15NO6/c1-19-11(15)7-10(12(16)17)14-13(18)20-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3,(H,14,18)(H,16,17)/t10-/m0/s1
InChI Key
PHMBNDDHIBIDRQ-JTQLQIEISA-N
Canonical SMILES
COC(=O)CC(C(=O)O)NC(=O)OCC1=CC=CC=C1

Aspartic acid N-[(phenylmethoxy)carbonyl]- 4-methyl ester, commonly known as a protected amino acid, plays a pivotal role in biochemical research and pharmaceutical development. Here are four key applications of Aspartic acid N-[(phenylmethoxy)carbonyl]- 4-methyl ester presented with high perplexity and burstiness:

Peptide Synthesis: This safeguarded variant of aspartic acid is indispensable in peptide synthesis, enabling the incorporation of aspartic acid residues sans undesirable side reactions. The carbobenzoxy (Cbz) group shields the amino group while the 4-methyl ester protects the carboxyl group, ensuring selective reactions during peptide chain elongation. Post-synthesis, these protective groups can be selectively removed under specific conditions to yield the desired peptide, facilitating precise molecular construction.

Pharmaceutical Development: Aspartic acid derivatives find utility in the formulation of peptide-based pharmaceuticals. The protective groups play a crucial role in stabilizing the molecule during chemical synthesis and pharmacokinetic investigations. This aids in the efficient production of bioactive peptides that can function as hormone analogs, enzyme inhibitors, or therapeutic agents across a spectrum of medical treatments, promising advancements in pharmaceutical innovation.

Structural Biology: Within the realm of structural biology, protected amino acids such as Aspartic acid N-[(phenylmethoxy)carbonyl]- 4-methyl ester are instrumental in exploring protein folding and interactions. These derivatives empower researchers to strategically introduce aspartic acid at specific sites within synthetic peptides or proteins. Through meticulous control of the protection and deprotection processes, scientists can probe the impact of aspartic acid on protein conformation and stability, offering insights into the intricacies of molecular structures.

Bioconjugation: This compound emerges as a valuable asset in bioconjugation methodologies where it facilitates the attachment of peptides or proteins to diverse molecules like fluorescent tags or drugs. The protective groups serve to thwart premature reactions, ensuring targeted conjugation at the desired site. This capability proves pivotal in crafting precise drug delivery systems, diagnostic tools, and other biotechnological applications, underscoring the versatility and utility of Aspartic acid N-[(phenylmethoxy)carbonyl]- 4-methyl ester in modern scientific endeavors.

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