Z-3-(1-naphthyl)-L-alanine
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Z-3-(1-naphthyl)-L-alanine

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Category
CBZ-Amino Acids
Catalog number
BAT-005743
CAS number
65365-15-3
Molecular Formula
C21H19NO4
Molecular Weight
349.37
Z-3-(1-naphthyl)-L-alanine
IUPAC Name
(2S)-3-naphthalen-1-yl-2-(phenylmethoxycarbonylamino)propanoic acid
Synonyms
Z-L-Ala(1-naphthyl)-OH; (2S)-2-([(Benzyloxy)carbonyl]amino)-3-naphthalen-1-ylpropanoic acid
Appearance
White to off-white solid
Purity
≥ 99% (HPLC)
Melting Point
136-168 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C21H19NO4/c23-20(24)19(22-21(25)26-14-15-7-2-1-3-8-15)13-17-11-6-10-16-9-4-5-12-18(16)17/h1-12,19H,13-14H2,(H,22,25)(H,23,24)/t19-/m0/s1
InChI Key
HNYQEAGTPQSPLT-IBGZPJMESA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CC2=CC=CC3=CC=CC=C32)C(=O)O

Z-3-(1-naphthyl)-L-alanine, a specialized amino acid with unique properties, finds valuable application in diverse scientific and industrial realms. Here are the key applications articulated with a high degree of perplexity and burstiness:

Protein Engineering: Incorporating Z-3-(1-naphthyl)-L-alanine into protein structures allows researchers to delve into protein folding stability and interactions. By substituting traditional amino acids with this naphthyl derivative, scientists can scrutinize changes in protein function and dynamics. This critical insight is pivotal for crafting proteins with tailored properties suitable for industrial and therapeutic purposes.

Fluorescent Probes: The naphthyl group present in Z-3-(1-naphthyl)-L-alanine imparts fluorescence attributes rendering it a valuable fluorescent probe in biochemical assays. Its application in labeling proteins and peptides facilitates visualizing and tracking these biomolecules in live cell imaging and other fluorescence-based methodologies. These utilities play a pivotal role in elucidating cellular processes and protein localization intricacies.

Peptide Synthesis: Playing a crucial role in peptide synthesis, Z-3-(1-naphthyl)-L-alanine acts as a fundamental building block for crafting bespoke peptides with specialized functionalities. Its incorporation in peptide chains confers distinctive hydrophobic and aromatic characteristics that influence interactions with biological membranes or proteins. This capability is particularly advantageous in designing peptide-based drugs with heightened specificity and efficacy.

Receptor Binding Studies: Z-3-(1-naphthyl)-L-alanine is instrumental in receptor binding assays aimed at investigating ligand-receptor interactions. Through integrating this amino acid into ligands, researchers can explore the binding affinity and specificity of receptors across diverse biological systems. These comprehensive studies offer invaluable insights into receptor functionality paving the way for the development of novel therapeutic agents targeting specific receptors.

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