3-(2-Naphthyl)-L-alanine
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3-(2-Naphthyl)-L-alanine

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Category
L-Amino Acids
Catalog number
BAT-007802
CAS number
58438-03-2
Molecular Formula
C13H13NO2
Molecular Weight
215.25
3-(2-Naphthyl)-L-alanine
IUPAC Name
(2S)-2-amino-3-naphthalen-2-ylpropanoic acid
Synonyms
L-Ala(2-naphthyl)-OH; (S)-2-Amino-3-naphthalen-2-yl-propionic acid; l-2-naphthylalanine; BETA-(2-NAPHTHYL)-ALANINE; H-2-Nal-OH; (2S)-2-amino-3-(2-naphthyl)propanoic acid; L-3-(2-Naphthyl)-alanine; 3-Naphthalen-2-ylalanine; beta-2-naphthyl-l-alanine; L-beta-(2-Naphthyl)alanine
Related CAS
122745-12-4 (hydrochloride)
Appearance
White or whitish powder
Purity
≥ 99% (Assay)
Density
1.254 g/cm3
Melting Point
240 °C (dec.)
Boiling Point
412.3 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H13NO2/c14-12(13(15)16)8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7,12H,8,14H2,(H,15,16)/t12-/m0/s1
InChI Key
JPZXHKDZASGCLU-LBPRGKRZSA-N
Canonical SMILES
C1=CC=C2C=C(C=CC2=C1)CC(C(=O)O)N

3-(2-Naphthyl)-L-alanine, an amino acid derivative with exceptional chemical characteristics, finds diverse scientific applications. Explore its key uses presented with high perplexity and burstiness:

Fluorescent Labeling: Delve into the world of protein and peptide research with 3-(2-Naphthyl)-L-alanine, a compound harnessed for fluorescent labeling experiments. Its naphthyl group emits robust fluorescence, facilitating the tracking of proteins and peptides within biological systems. This application offers a valuable lens into studying protein dynamics, interactions, and localization in real-time scenarios.

Enzyme Substrate Studies: Unlock the potential of this compound as a crucial substrate in biochemical assays for various enzymes. By integrating 3-(2-Naphthyl)-L-alanine into enzyme studies, researchers gain insights into enzyme specificity, kinetics, and mechanisms of action. These revelations play a pivotal role in drug discovery and enhancing our understanding of enzyme functions within metabolic pathways.

Pharmaceutical Development: Embark on a journey through pharmaceutical research with 3-(2-Naphthyl)-L-alanine, exploring its unique structure and potential therapeutic attributes. This compound serves not only as a cornerstone for peptide-based drugs but also holds promise for anti-inflammatory or anticancer treatments. Furthermore, it enables the design of peptide drugs with heightened stability and bioavailability, shaping the landscape of pharmaceutical innovation.

Structural Biology: Dive deep into the realm of structural biology using 3-(2-Naphthyl)-L-alanine for crystallographic studies involving peptides and proteins. The distinctive electron density provided by the naphthyl group aids in unraveling the complex structures of biomolecules, shedding light on protein structure-function relationships. This application serves as a cornerstone in designing structure-based drugs and advancing our understanding of biological complexities.

1.Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts.
Hori M1, Sakakura A, Ishihara K. J Am Chem Soc. 2014 Sep 24;136(38):13198-201. doi: 10.1021/ja508441t. Epub 2014 Sep 16.
We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-l-alanine amide. The asymmetric environment created by intramolecular π-cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.
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