55516-54-6

Usage

Uses

Used in Organic Synthesis:
L-1-Naphthylalanine is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, L-1-Naphthylalanine is utilized as a building block for the development of novel drugs, thanks to its unique chemical properties that can be exploited in drug design and synthesis.
Used in Agrochemicals:
L-1-Naphthylalanine is employed as a vital component in the formulation of agrochemicals, such as pesticides and herbicides, due to its ability to enhance the effectiveness of these products.
Used in Dyestuff Industry:
L-1-Naphthylalanine is also used as an intermediate in the production of dyes, where its distinctive chemical properties contribute to the creation of vibrant and long-lasting colorants for various applications.

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 
• 136015-49-1 2-Acetylamino-2-naphthalen-1-ylmethyl-malonic acid monoethyl ester 
• 125761-75-3 2-Acetylamino-3-naphthalen-1-yl-propionic acid ethyl ester 
• 3163-27-7 2-(bromomethyl)naphthalene 
• 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 
• 96402-49-2 N^α-Fmoc-3-(1'-naphthyl)alanine 
• 119357-91-4 (S)-1-naphthylalanine methyl ester 
• 118586-12-2 N--L-norleucine 
• 141714-15-0 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(naphthalen-1-yl)propanamido)hexanoate 
• 141713-89-5 {(S)-1-[(S)-1-((1S,2S)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-butylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-90-8 {(S)-1-[(S)-1-((1S,2S)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-pentylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 118586-21-3 {(S)-1-[(S)-1-((1S,2S,4S)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-5-methyl-hexylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-91-9 {(S)-1-[(S)-1-((1S,2S,4R)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-92-0 {(S)-1-[(S)-1-((1S,2S,4R)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-6-methyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 118586-64-4 {(S)-1-[(S)-1-((1S,2S,4R)-2,6-Dihydroxy-1-isobutyl-4-isobutylcarbamoyl-hexylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-94-2 {(S)-1-[(S)-1-((1S,2S)-7-Amino-2-hydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 118609-75-9 {(S)-1-[(S)-1-((1S,2S)-2,6-Dihydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 118586-63-3 {(S)-1-[(S)-1-((1S,2S,4R)-2,7-Dihydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 

Relevant academic research and scientific papers

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.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

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.

Chiral salen-metal complexes as novel catalysts for the asymmetric synthesis of α-amino acids under phase transfer catalysis conditions

Chiral salen-metal complexes have been tested as catalysts for the C-alkylation of Schiff's bases of alanine and glycine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1-10 mol% of the catalyst). The best catalyst, which was derived from a Cu(II) complex of (1R, 2R or 1S,2S)-[N,N′-bis(2′-hydroxybenzylidene)]-1,2-diaminocyclohexane, gave α-amino and α-methyl-α-amino acids with enantiomeric excesses of 70-96%.

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.

Renin inhibitors. I. Synthesis and structure-activity relationship of transition-state inhibitors containing homostatine analogues at the scissile bond

The synthesis and structure-activity relationships of transition-state renin inhibitors containing the homostatine analogues at the scissile bond are described. These inhibitors incorporate the amino acid side chains corresponding to positions 7-12 (Psub

Synthesis and biological activities of cholecystokinin analogues substituted in position 30 by 3-(1-naphthyl)-L-alanine [Nal(1)] or 3-(2-naphthyl)-L-alanine [Nal(2)]

Acetyl derivatives of ethyl esters of 3-(1-naphthyl)-D,L-alanine and 3-(2-naphthyl)-D,L-alanine were synthesized through a malonic condensation. Resolution of these derivatives by subtilisin Carlsberg followed by acid hydrolysis afforded the 2 optical isomers of 3-(1-naphthyl)-alanine [Nal(1)] and 3-(2-naphthyl)-alanine [Nal(2)]. The L enantiomers of these amino acids were incorporated into the sequence of cholecystokinin in place of the tryptophan in position 30. The cholecystokinin analogues thus obtained behaved as full agonists, with reduced potencies on rat pancreatic acini and on guinea pig brain membranes, by about one order of magnitude for the Nal(1) derivative, as compared to the potent parent compound Boc-Tyr(SO3H)-Nle-Gly-Trp-Nle-Asp-Phe-NH2.