(S)-2-Amino-3-(naphthalen-2-yl)propanoic acid, CAS No. 58438-03-2

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58438-03-2

Catalog No. EBD2156819

CAS 58438-03-2

Name (S)-2-Amino-3-(naphthalen-2-yl)propanoic acid

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Basic Information

Synonyms: H-2-Nal-OH L-2-Naphthylalanine 3-(2-Naphthyl)-L-alanine 2-L-naphtylalanine L-3-(2-Naphthyl)-alanine (S)-2-Amino-3-(naphthalen-2-yl)propanoicacid L-3-(2-naphthyl)alanine Naphthylalanine l-2-nal-oh l-2-napthylalanine 2-naphthyl-l-alanine 3-naphth-2-yl-l-alanine l-3-(2-naphtyl)-alanine h-3-l-ala(2-naphthyl)-oh 3-naphth-2-yl-l-phenylalanine 1-(s)-amino-2-naphthalenepropanoicacid (s)-2-amino-3-(2-naphthyl)propanoicacid (2s)-2-amino-3-(2-naphthyl)propanoicacid (2s)-2-amino-3-(2-naphthyl)propionicacid

Molecular Formula: C13H13NO2

Molecular Weight: 215.25

MDL Number: MFCD00066087

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates

Product Description:

3-(2-Naphthyl)-L-alanine is a non-proteinogenic amino acid derivative characterized by the presence of a 2-naphthyl group attached to the beta-carbon of the L-alanine backbone. This structure imparts unique steric and hydrophobic properties compared to natural aromatic amino acids like phenylalanine or tryptophan. Its primary application is in the field of peptide chemistry and medicinal research. It serves as a crucial building block for the synthesis of modified peptides and peptidomimetics. Incorporating this unnatural amino acid into peptide sequences can significantly alter the peptide's conformation, stability, binding affinity, and metabolic profile, making it valuable for developing novel therapeutic agents, enzyme inhibitors, and biochemical probes. Its chiral nature (L-configuration) is essential for maintaining biological activity in many peptide-based applications. This compound is also utilized in materials science for constructing functional organic frameworks and in asymmetric synthesis as a chiral auxiliary or ligand precursor due to its rigid, bulky naphthyl group. It is typically handled as a white to off-white crystalline powder and requires standard precautions for handling amino acids and organic compounds.

Physical Properties

Melting Point: 240-253 °C

Boiling Point: 412.3 °C at 760 mmHg

Flash Point: 203.2 °C

Density: 1.254 g/cm3

Storage: 2-8°C

Analytical Data

Appearance: off-white crystalline powder