N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine
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N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine

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Category
BOC-Amino Acids
Catalog number
BAT-005198
CAS number
219297-10-6
Molecular Formula
C19H23NO4
Molecular Weight
329.39
N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine
IUPAC Name
(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-naphthalen-2-ylbutanoic acid
Synonyms
Boc-D-Ala(2-Naph)-(C#CH2)OH; Boc-D-Nal(2)-(C#CH2)OH; (R)-3-[(t-Butoxycarbonyl)amino]-4-(2-naphthyl)butanoic acid; Boc-(R)-3-amino-4-(2-naphthyl)-butyric acid; (R)-3-(tert-butoxycarbonylamino)-4-(naphthalen-2-yl)butanoic acid; Boc-(2-naphthyl)-D-β-homoalanine; Boc-D-β-HomoAla(2-naphthyl)-OH
Appearance
White to off-white powder
Purity
98-100% (HPLC)
Density
1.179 g/cm3
Melting Point
156-162 °C
Boiling Point
527.9 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C19H23NO4/c1-19(2,3)24-18(23)20-16(12-17(21)22)11-13-8-9-14-6-4-5-7-15(14)10-13/h4-10,16H,11-12H2,1-3H3,(H,20,23)(H,21,22)/t16-/m1/s1
InChI Key
RKULNBHGHIPRGC-MRXNPFEDSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC2=CC=CC=C2C=C1)CC(=O)O

N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine, a specialty amino acid derivative with a wide array of applications in chemical and biochemical research, possesses unique characteristics that lend themselves to diverse uses. Here are the key applications, presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental component in peptide synthesis, N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine plays a crucial role in constructing peptide chains. Its distinctive structure facilitates the incorporation of naphthyl groups into peptides, imparting beneficial attributes such as heightened hydrophobicity and enhanced binding affinity. This feature proves invaluable in crafting peptides tailored for drug development and studies on protein interactions, showcasing the versatility of this compound in the realm of biochemistry.

Protein Engineering: Through the integration of this compound into proteins, researchers can manipulate and engineer proteins to exhibit modified characteristics. By replacing specific amino acids with N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine, scientists can investigate the effects on protein folding, stability, and functionality. This application is essential for unraveling the intricate relationships between protein structure and function, paving the way for the creation of novel proteins endowed with desired attributes, illustrating the power of this amino acid derivative in protein engineering endeavors.

Pharmaceutical Research: A pivotal player in drug discovery, N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine finds utility in developing peptide-based therapeutic agents. Its incorporation enhances the pharmacokinetic and pharmacodynamic properties of peptide drugs, lending them attributes such as increased resistance to enzymatic degradation and improved membrane permeability. This compound emerges as a valuable asset in creating more potent and stable peptide medications, underscoring its significance in advancing pharmaceutical research and development.

Bioconjugation Studies: Beyond its role in peptide and protein applications, this amino acid derivative finds a niche in bioconjugation studies, where it is utilized to link peptides and proteins with various molecules, like drugs, imaging agents, or polymers. The distinctive naphthyl group offers a unique site for selective conjugation chemistry, enabling the creation of multifunctional biomolecules tailored for targeted drug delivery, diagnostic imaging, and other biomedical applications. This application underscores the versatility and adaptability of N-β-(t-Butoxycarbonyl)-γ-(2-naphthyl)-D-β-homoalanine in facilitating innovative bioconjugation strategies, showcasing its potential in expanding the horizons of biochemical research and development.

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