N-β-(t-Butoxycarbonyl)-γ-(1-naphthyl)-D-β-homoalanine
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N-β-(t-Butoxycarbonyl)-γ-(1-naphthyl)-D-β-homoalanine

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Category
BOC-Amino Acids
Catalog number
BAT-005194
CAS number
190190-49-9
Molecular Formula
C19H23NO4
Molecular Weight
329.39
N-β-(t-Butoxycarbonyl)-γ-(1-naphthyl)-D-β-homoalanine
IUPAC Name
(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-naphthalen-1-ylbutanoic acid
Synonyms
Boc-D-Ala(1-Naph)-(C#CH2)OH; Boc-D-Nal(1)-(C#CH2)OH; (R)-3-[(t-Butoxycarbonyl)amino]-4-(1-naphthyl)butanoic acid; Boc-(R)-3-Amino-4-(1-naphthyl)butyric acid; Boc-D-b-HoAla(1-naphthyl)-OH; (R)-3-(Boc-amino)-4-(1-naphthyl)butyric acid; Boc-(1-naphthyl)-D-ß-homoalanine
Appearance
White solid
Purity
≥ 98% (HPLC)
Density
1.179 g/cm3
Boiling Point
527.9±43.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C19H23NO4/c1-19(2,3)24-18(23)20-15(12-17(21)22)11-14-9-6-8-13-7-4-5-10-16(13)14/h4-10,15H,11-12H2,1-3H3,(H,20,23)(H,21,22)/t15-/m1/s1
InChI Key
JXDXPRAUFACOHG-OAHLLOKOSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC=CC2=CC=CC=C21)CC(=O)O

N-β-(t-Butoxycarbonyl)-γ-(1-naphthyl)-D-β-homoalanine, a synthetic amino acid derivative, finds diverse applications in biochemical and pharmaceutical research. Here are the key applications, presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental building block in peptide synthesis, this compound enables the creation of intricate peptide structures. Its unique composition permits the integration of non-standard amino acids into peptide chains, expanding the repertoire of synthetic peptides. Such alterations can result in peptides exhibiting enhanced stability, activity, and specificity, catering to both research and therapeutic endeavors.

Protein Engineering: Through the strategic inclusion of N-β-(t-Butoxycarbonyl)-γ-(1-naphthyl)-D-β-homoalanine in proteins, researchers can delve into the intricate relationships between structure and function. By substituting this amino acid at specific sites, scientists can decipher changes in protein folding, stability, and molecular interactions. This innovative approach is particularly valuable for designing proteins with novel functionalities or enhanced attributes, paving the way for advanced therapeutic applications.

Drug Development: Leveraging its distinctive structural properties, this compound emerges as a promising candidate for the development of novel pharmaceutical agents. By integrating it into drug molecules, researchers can optimize pharmacokinetic parameters such as absorption, distribution, and metabolic stability. This integration serves as a powerful tool in medicinal chemistry, facilitating the creation of drugs with heightened efficacy and reduced adverse effects, thereby propelling drug development into new frontiers.

Fluorescent Probes: The presence of the naphthyl group in N-β-(t-Butoxycarbonyl)-γ-(1-naphthyl)-D-β-homoalanine imparts fluorescent properties, rendering it invaluable in diverse bioimaging applications. Researchers can utilize this compound as a fluorescent marker to label proteins or peptides, enabling real-time tracking of biological processes. This capability facilitates in-depth exploration of dynamic cellular events and protein localization within live cells, offering unprecedented insights into the dynamic nature of biological systems.

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