N-β-(9-Fluorenylmethoxycarbonyl)-γ-(1-naphthyl)-L-β-homoalanine
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N-β-(9-Fluorenylmethoxycarbonyl)-γ-(1-naphthyl)-L-β-homoalanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-004689
CAS number
270063-38-2
Molecular Formula
C29H25NO4
Molecular Weight
451.52
N-β-(9-Fluorenylmethoxycarbonyl)-γ-(1-naphthyl)-L-β-homoalanine
IUPAC Name
(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-naphthalen-1-ylbutanoic acid
Synonyms
Fmoc-Ala(1-Naph)-(C#CH2)OH; Fmoc-Nal(1)-(C#CH2)OH; (S)-3-[(9-Fluorenylmethoxycarbonyl)amino]-4-(1-naphthyl)butanoic acid
Appearance
White powder
Purity
≥ 98%
Density
1.275g/cm3
Boiling Point
702.5°C at 760mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C29H25NO4/c31-28(32)17-21(16-20-10-7-9-19-8-1-2-11-22(19)20)30-29(33)34-18-27-25-14-5-3-12-23(25)24-13-4-6-15-26(24)27/h1-15,21,27H,16-18H2,(H,30,33)(H,31,32)/t21-/m0/s1
InChI Key
QKDVUQGMQTZWKV-NRFANRHFSA-N
Canonical SMILES
C1=CC=C2C(=C1)C=CC=C2CC(CC(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

N-β-(9-Fluorenylmethoxycarbonyl)-γ-(1-naphthyl)-L-β-homoalanine, commonly known as Fmoc-Nal-OH, is a synthetic amino acid derivative utilized in peptide synthesis and various biochemical applications. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Embracing solid-phase peptide synthesis (SPPS), researchers leverage Fmoc-Nal-OH to insert naphthylalanine residues into peptides, augmenting their structural and functional characteristics. This strategic modification empowers scientists to craft peptides with enhanced stability, bioavailability, and target specificity, propelling advancements in peptide design.

Protein Engineering: Delving into the realm of protein engineering, scientists harness Fmoc-Nal-OH to engineer modified proteins imbued with novel functionalities or enhanced properties. By integrating this non-natural amino acid, proteins can acquire unique attributes absent in their natural forms. This application proves invaluable in the development of therapeutic proteins and enzymes with enhanced performance, driving innovation in protein design.

Pharmacological Studies: Infusing peptides and small proteins with Fmoc-Nal-OH enables researchers to explore their interactions with key biological targets like receptors and enzymes. Through structural modifications using this synthetic amino acid, scientists probe binding affinities, specificities, and mechanisms of action—pivotal insights essential for the advancement of drug discovery and development, unlocking new possibilities in pharmacology.

Bioconjugation: Harnessing bioconjugation techniques, Fmoc-Nal-OH serves as a crucial element in linking peptides and proteins with diverse molecules such as drugs, fluorescent probes, or nanoparticles. This approach underpins the creation of targeted therapeutics and imaging agents, amplifying efficacy and specificity. By attaching Fmoc-Nal-OH-modified peptides to these molecules, researchers craft multifunctional bioconjugates with heightened therapeutic potential, ushering in a new era of precision bioconjugation.

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