Fmoc-3-(2-naphthyl)-L-alanine
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Fmoc-3-(2-naphthyl)-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007315
CAS number
112883-43-9
Molecular Formula
C28H23NO4
Molecular Weight
437.49
Fmoc-3-(2-naphthyl)-L-alanine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-2-ylpropanoic acid
Synonyms
Fmoc-L-Ala(2-naphthyl)-OH
Related CAS
138774-94-4 (D-isomer)
Appearance
White powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.296 g/cm3
Melting Point
155 °C
Boiling Point
690.7°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C28H23NO4/c30-27(31)26(16-18-13-14-19-7-1-2-8-20(19)15-18)29-28(32)33-17-25-23-11-5-3-9-21(23)22-10-4-6-12-24(22)25/h1-15,25-26H,16-17H2,(H,29,32)(H,30,31)/t26-/m0/s1
InChI Key
JYUTZJVERLGMQZ-SANMLTNESA-N
Canonical SMILES
C1=CC=C2C=C(C=CC2=C1)CC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35

Fmoc-3-(2-naphthyl)-L-alanine is a derivative of alanine commonly used in peptide synthesis and other biochemical applications. Here are some key applications of Fmoc-3-(2-naphthyl)-L-alanine:

Peptide Synthesis: Fmoc-3-(2-naphthyl)-L-alanine is often used as a building block in solid-phase peptide synthesis. Its unique naphthyl group can introduce aromaticity and hydrophobicity to peptides, which might be critical for the biological activity or structure of the synthesized peptides. This makes it an essential tool in the development of peptide-based drugs and studies involving peptide-protein interactions.

Fluorescence Studies: Due to its aromatic naphthyl group, Fmoc-3-(2-naphthyl)-L-alanine can be used in fluorescence-based biochemical assays. This can help in tracking and analyzing the behavior of peptides and proteins in different environments. The compound's fluorescence properties enable highly sensitive and specific detection in various research settings.

Protein Engineering: Fmoc-3-(2-naphthyl)-L-alanine can be integrated into proteins to study protein folding, structure, and interactions. By incorporating this non-natural amino acid, researchers can explore how substitutions affect protein function and stability. These insights are critical for rational protein design and engineering efforts.

Structural Biology: Fmoc-3-(2-naphthyl)-L-alanine is useful in structural biology for the design of peptides that can form stable secondary structures such as alpha-helices and beta-sheets. Its unique side chain can influence the folding patterns and stability of these structures. This application is particularly valuable in the study of protein conformations and the development of biomimetic materials.

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