3-(1-Naphthyl)-D-alanine
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3-(1-Naphthyl)-D-alanine

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Category
D-Amino Acids
Catalog number
BAT-007797
CAS number
78306-92-0
Molecular Formula
C13H13NO2
Molecular Weight
215.25
3-(1-Naphthyl)-D-alanine
IUPAC Name
(2R)-2-amino-3-naphthalen-1-ylpropanoic acid
Synonyms
D-3-Ala(1-naphthyl)-OH; (R)-2-Amino-3-(naphthalen-1-yl)propanoic acid; D-1-Naphthylalanine; (R)-2-AMINO-3-(NAPHTHALEN-1-YL)PROPANOIC ACID; H-D-1-Nal-OH; 3-(1-NAPHTHYL)-D-ALA; (2R)-2-amino-3-(naphthalen-1-yl)propanoic acid
Related CAS
122745-09-9 (hydrochloride)
Appearance
Off-white powder
Purity
≥ 98% (HPLC)
Density
1.254±0.06 g/cm3 (Predicted)
Melting Point
215-219 °C
Boiling Point
412.3±33.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H13NO2/c14-12(13(15)16)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7,12H,8,14H2,(H,15,16)/t12-/m1/s1
InChI Key
OFYAYGJCPXRNBL-GFCCVEGCSA-N
Canonical SMILES
C1=CC=C2C(=C1)C=CC=C2CC(C(=O)O)N

3-(1-Naphthyl)-D-alanine is a chemical compound with distinct enantiomeric properties, serving a multitude of purposes in scientific research and industrial applications. Here are the key applications presented with high perplexity and burstiness:

Chiral Compound Synthesis: Acting as a fundamental building block, 3-(1-Naphthyl)-D-alanine plays a pivotal role in synthesizing chiral compounds vital for pharmaceuticals and agrochemicals. Its specific stereochemistry facilitates the creation of enantiomerically pure drugs, ensuring heightened effectiveness and decreased side effects. Researchers leverage this compound to cultivate enantiomer-specific reactions, revolutionizing chemical synthesis methodologies.

Enzyme Inhibitor Studies: Employed as an inhibitory agent in enzymatic investigations, 3-(1-Naphthyl)-D-alanine serves as a competitive inhibitor, enabling scientists to delve into the intricacies of enzyme-substrate interactions. By utilizing this compound, researchers dissect the kinetics and mechanisms governing diverse enzymes, laying the groundwork for novel drug discovery approaches and the advancement of enzyme-targeted therapies.

Fluorescence Studies: With its distinctive naphthyl group, 3-(1-Naphthyl)-D-alanine showcases fluorescence characteristics, rendering it invaluable for biochemical assays. Incorporated into proteins or peptides, it facilitates the monitoring of biochemical interactions through fluorescence spectroscopy. This application proves instrumental in cellular and molecular biology endeavors, shedding light on molecular dynamics and binding phenomena with pinpoint accuracy.

Peptide-Based Drug Design: Integral to the realm of peptide-based drug development, 3-(1-Naphthyl)-D-alanine contributes significantly to the bioactivity and stability of peptide therapeutics through its unique structural attributes. By integrating this amino acid into peptide chains, researchers elevate the pharmacological properties of peptide-based treatments, spearheading the creation of innovative therapies for diverse medical conditions, marking a paradigm shift in the field of medicine and therapeutic interventions.

1.[D-1-Nal4]endomorphin-2 is a potent micro-opioid receptor antagonist in the aequorin luminescence-based calcium assay.
Fichna J1, Piestrzeniewicz M, Gach K, Poels J, Burgeon E, Vanden Broeck J, Janecka A. Life Sci. 2006 Aug 8;79(11):1094-9. Epub 2006 Mar 21.
A functional assay, based on aequorin-derived luminescence triggered by receptor-mediated changes in Ca(2+) levels, was used to examine relative potency and efficacy of the micro-opioid receptor antagonists. A series of position 3- and 4-substituted endomorphin-2 (Tyr-Pro-Phe-Phe-NH(2)) analogues containing D-3-(1-naphthyl)-alanine (D-1-Nal) or D-3-(2-naphthyl)-alanine (D-2-Nal), which were previously shown to reverse antinociception induced by endomorphin-2 in the in vivo hot-plate test in mice, was tested in the aequorin luminescence-based calcium assay to examine their micro-opioid antagonist potency in vitro. A recombinant mammalian cell line expressing the micro-opioid receptor together with a luminescent reporter protein, apoaequorin, was used in the study. The results obtained in this functional assay indicated that analogues with D-1-Nal or D-2-Nal substitutions in position 4 of endomorphin-2 are strong micro-opioid receptor antagonists, while those substituted in position 3 are partial agonists.
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