Fmoc-3-(9-anthryl)-L-alanine
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Fmoc-3-(9-anthryl)-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007326
CAS number
268734-27-6
Molecular Formula
C32H25NO4
Molecular Weight
487.55
Fmoc-3-(9-anthryl)-L-alanine
IUPAC Name
(2S)-3-anthracen-9-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-3-Ala(9-anthryl)-OH
Related CAS
268733-63-7 (D-isomer)
Appearance
Yellow solid
Purity
≥ 98% (Chiral HPLC)
Density
1.311 g/cm3
Boiling Point
756.3°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C32H25NO4/c34-31(35)30(18-28-22-11-3-1-9-20(22)17-21-10-2-4-12-23(21)28)33-32(36)37-19-29-26-15-7-5-13-24(26)25-14-6-8-16-27(25)29/h1-17,29-30H,18-19H2,(H,33,36)(H,34,35)/t30-/m0/s1
InChI Key
OGLRHZZGDZRSHK-PMERELPUSA-N
Canonical SMILES
C1=CC=C2C(=C1)C=C3C=CC=CC3=C2CC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Fmoc-3-(9-anthryl)-L-alanine, a fluorescent amino acid derivative, finds widespread use in peptide synthesis and diverse biochemical applications. Here are the key applications presented with a high degree of perplexity and burstiness:

Fluorescent Labeling: Serving as a potent fluorophore, Fmoc-3-(9-anthryl)-L-alanine acts as a luminescent marker in peptides and proteins, enabling the exploration of their spatial localization, molecular interactions, and biological functions within intricate systems. The aromatic anthryl moiety emits intense fluorescence, empowering researchers to visualize and track peptides with precision under the lens of a fluorescence microscope. This tool proves invaluable in cellular imaging, facilitating real-time monitoring of dynamic biological processes with remarkable clarity.

Peptide Synthesis: Integral to solid-phase peptide synthesis (SPPS), this compound assumes a pivotal role as a foundational unit for constructing fluorescent peptides. Fmoc-3-(9-anthryl)-L-alanine seamlessly integrates into peptide chains, facilitating the tailored synthesis of bespoke peptides endowed with specific fluorescent characteristics. These fluorescent peptide constructs serve as indispensable instruments for probing intricate protein-protein and protein-ligand interactions, unveiling insights into molecular binding dynamics with unparalleled detail.

Biophysical Studies: Unveiling the dynamic intricacies of peptide and protein folding pathways, Fmoc-3-(9-anthryl)-L-alanine emerges as a crucial asset in biophysical investigations. The unique fluorescence signature of this amino acid derivative enables researchers to surveil real-time conformational alterations, shedding light on crucial aspects of protein stability, folding kinetics, and the cascade of events in misfolding-related afflictions like Alzheimer's disease. This real-time monitoring capability empowers scientists with invaluable insights into the structural dynamics governing protein function and malfunction.

Drug Delivery Research: Stepping into the realm of drug delivery exploration, Fmoc-3-(9-anthryl)-L-alanine can be harnessed as a strategic component in peptide-based systems to scrutinize their delivery kinetics, cellular uptake mechanisms, and distribution profiles. The incorporation of this fluorescent tag aids in tracking the journey and release of peptide-based therapeutics within live cellular environments or animal models. This real-time visualization capability serves as a cornerstone for refining drug delivery architectures, optimizing therapeutic dispersion patterns, and elevating the efficacy of drug delivery systems to new heights of precision and impact.

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