N-β-(9-Fluorenylmethoxycarbonyl)-γ-(2-naphthyl)-L-β-homoalanine
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N-β-(9-Fluorenylmethoxycarbonyl)-γ-(2-naphthyl)-L-β-homoalanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001822
CAS number
1186216-21-6
Molecular Formula
C29H25NO4
Molecular Weight
451.52
IUPAC Name
(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-naphthalen-2-ylbutanoic acid
Synonyms
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(naphthalen-2-yl)butanoic acid; (S)-3-(Fmoc-amino)-4-(2-naphthyl)butyric acid; Fmoc-beta-2-Homonal-OH; Fmoc-(S)-3-Amino-4-(2-naphthyl)butyric acid; Fmoc-Ala(2-Naph)-OH; Fmoc-Nal(2)-OH; (S)-3-[(9-Fluorenylmethoxycarbonyl)amino]-4-(2-naphthyl)butanoic acid
InChI
InChI=1S/C29H25NO4/c31-28(32)17-22(16-19-13-14-20-7-1-2-8-21(20)15-19)30-29(33)34-18-27-25-11-5-3-9-23(25)24-10-4-6-12-26(24)27/h1-15,22,27H,16-18H2,(H,30,33)(H,31,32)/t22-/m0/s1
InChI Key
LQGDRWACMZMSCD-QFIPXVFZSA-N
Canonical SMILES
C1=CC=C2C=C(C=CC2=C1)CC(CC(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

N-β-(9-Fluorenylmethoxycarbonyl)-γ-(2-naphthyl)-L-β-homoalanine, a synthetic derivative of an amino acid, is extensively utilized in peptide synthesis across various research domains. Here are the key applications, presented with high perplexity and burstiness:

Peptide Synthesis: Serving as an essential component in solid-phase peptide synthesis (SPPS), this compound assumes a critical role as a foundational building block. The fluorenylmethoxycarbonyl (Fmoc) group acts as a crucial protective shield for the amino function during the methodical stepwise assembly of peptides. Its incorporation ensures the efficient and precise synthesis of intricate peptides, tailored for both research endeavors and therapeutic interventions.

Drug Development: In the realm of drug discovery innovation, N-β-(9-Fluorenylmethoxycarbonyl)-γ-(2-naphthyl)-L-β-homoalanine emerges as a key player in formulating peptide-based drug candidates. By integrating this synthetic amino acid into peptides, researchers have the ability to finely adjust their biological properties, bolstering stability and enhancing therapeutic efficacy. This strategic utilization plays a pivotal role in sculpting and optimizing peptide-based therapies for a diverse array of medical conditions.

Protein-Protein Interaction Studies: Venturing into the domain of biochemical investigations, this compound assumes a critical role in elucidating complex protein-protein interactions. Through the strategic incorporation of N-β-(9-Fluorenylmethoxycarbonyl)-γ-(2-naphthyl)-L-β-homoalanine into peptides or proteins, scientists can uncover binding affinities, decode interaction dynamics, and reveal structural conformations. These undertakings shed light on the intricate molecular cascades dictating cellular processes, pinpointing potential targets for therapeutic interventions.

Fluorescence Spectroscopy: Exploiting the fluorescent properties of the naphthyl group within N-β-(9-Fluorenylmethoxycarbonyl)-γ-(2-naphthyl)-L-β-homoalanine, researchers tap into its capabilities for fluorescence-based assays. By labeling peptides or proteins with this compound, scientists embark on tracking and imaging endeavors crucial for scrutinizing biomolecular interactions and deciphering cellular localizations, particularly in the dynamic realm of live-cell imaging experiments.

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