55516-54-6

Basic information

• Product Name: L-1-Naphthylalanine
• Synonyms: (S)-ALPHA-AMINO-1-NAPHTHALENEPROPANOIC ACID;(S)-(-)-AMINO-3-(1-NAPHTHYL) PROPANOIC ACID;(S)-2-AMINO-3-(NAPHTHALEN-1-YL)PROPANOIC ACID;(S)-2-AMINO-3-NAPHTHALEN-1-YL-PROPIONIC ACID;RARECHEM BK PT 0091;H-1-NAL-OH;H-ALA(1-NAPH)-OH;H-ALA(1-NAPHTHYL)-OH
• CAS NO: 55516-54-6
• Molecular Formula: C₁₃H₁₃NO₂
• Molecular Weight: 215.25
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Alanine [Ala, A];Unusual Amino Acids;a-amino
• Mol File: 55516-54-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 254-257 °C
• Boiling Point: 355.53°C (rough estimate)
• Flash Point: 203.2 °C
• Appearance: /Solid
• Density: 1.1242 (rough estimate)
• Vapor Pressure: 1.14E-08mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• PKA: 2.21±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: L-1-Naphthylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: L-1-Naphthylalanine(55516-54-6)
• EPA Substance Registry System: L-1-Naphthylalanine(55516-54-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 55516-54-6(Hazardous Substances Data)

Usage

Chemical Properties

white to very slightly beige powder

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

InChI:InChI=1/C13H13NO2/c1-9(13(15)16)14-12-8-4-6-10-5-2-3-7-11(10)12/h2-9,14H,1H3,(H,15,16)/t9-/m0/s1

Upstream product

• 59759-78-3 2-benzoylamino-3-naphthalen-1-yl-propionic acid 
• 56-40-6 glycine 
• 86-52-2 1-Chloromethylnaphthalene 
• 28095-56-9 2-amino-3-(1-naphthyl)propanoic acid 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 125761-75-3 2-Acetylamino-3-naphthalen-1-yl-propionic acid ethyl ester 
• 136015-49-1 2-Acetylamino-2-naphthalen-1-ylmethyl-malonic acid monoethyl ester 
• 5440-57-3 diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate 
• 51684-92-5 (S)-2-Acetylamino-3-naphthalen-1-yl-propionic acid 

Downstream Products

• 55447-00-2 (S)-2-tert-butoxycarbonylamino-3-naphthalen-1-yl-propionic acid 
• 136015-53-7 (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid 
• 136015-52-6 (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester 
• 136039-63-9 (S)-3-{(S)-2-[(S)-2-(2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-naphthalen-1-yl-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid 
• 136015-56-0 (S)-3-{(S)-2-[(S)-2-(2-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-naphthalen-1-yl-propionylamino]-hexanoylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid 
• 148452-17-9 3,5-dimethylbenzyl (2S)-2-t-butyloxycarbonylamino-3-(1-naphthyl)propionate 

Relevant articles and documents

Asymmetric synthesis of (S)-2-amino-3-(1-naphthyl)propanoic acid via chiral nickel complex. Crystal structure, circular dichroism, 1H and 13C NMR spectra of the complex

The recently published environmentally friendly preparation of a glycine synthon 2 from regeneratable chiral auxiliary BPB ((S)-N-(2-benzoylphenyl)- N′-benzylprolinamide) was used for preparative asymmetric synthesis of the non-coded amino acid 3-(1-naphthyl)alanine (1). Full assignment of 1H and 13C NMR of both intermediate complex 3 and 1 and X-ray structure determination of complex 3 were made. Cotton effects observed in circular dichroism spectrum of complex 3 are consistent with published empirical rules.

Enzymatic conversion of unnatural amino acids by yeast D-amino acid oxidase

Unnatural amino acids, particularly synthetic α-amino acids, are becoming crucial tools for modern drug discovery research. In particular, this application requires enantiomerically pure isomers. In this work we report on the resolution of racemic mixtures of the amino acids D,L-naphthylalanine and D,L-naphthylglycine by using a natural enzyme, D-amino acid oxidase from the yeast Rhodotorula gracilis. A significant improvement of the bioconversion is obtained using a single-point mutant enzyme designed by a rational approach. With this D-amino acid oxidase variant the complete resolution of all the unnatural amino acids tested was obtained: in this case, the bioconversion requires a shorter time and a lower amount of biocatalyst compared to the wild-type enzyme. The simultaneous production of the corresponding α-keto acid, a possible precursor of the amino acid in the L-form, improves the significance of the procedure.

Substituted quinoxaline-2-ones as glutamate receptor antagonists

A novel series of substituted quinoxaline 2-ones useful as neuroprotective agents are taught. Novel intermediates, processes of preparation, and pharmaceutical compositions containing the compounds are also taught. The compounds are glutamate receptor antagonists and are useful in the treatment of stroke, cerebral ischemia, or cerebral infarction resulting from thromboembolic or hemorrhagic stroke, cerebral vasospasms, hypoglycemia, cardiac arrest, status epilepticus, perinatal asphyxia, anoxia, seizure disorders, pain, Alzheimer's, Parkinson's, and Huntington's Diseases.