58438-04-3

Basic information

• Product Name: Boc-3-(2-Naphthyl)-L-alanine
• Synonyms: BOC-ALA(2-NAPH)-OH;BOC-ALA(2-NAPHTHYL)-OH;BOC-ALA-BETA-(2-NAPHTHYL)-OH;BOC-2-NAL-OH;BOC-2-L-NAPHTHYLALANINE;BOC-3-(2-NAPHTHYL)-ALANINE;BOC-3-(2-NAPHTHYL)-L-ALANINE;N-BOC-3-(2-NAPHTHYL)-L-ALANINE
• CAS NO: 58438-04-3
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36
• Product Categories: Amino Acids;Alanine [Ala, A];Unusual Amino Acids;Boc-Amino acid series;a-amino
• Mol File: 58438-04-3.mol

Chemical Properties

• Melting Point: 92-95 °C(lit.)
• Boiling Point: 454.92°C (rough estimate)
• Flash Point: 263.6 °C
• Appearance: Off-white/Solid
• Density: 1.2164 (rough estimate)
• Vapor Pressure: 2.58E-11mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• Storage Temp.: −20°C
• Solubility: soluble in Ethanol
• PKA: 3.88±0.30(Predicted)
• BRN: 4326467
• CAS DataBase Reference: Boc-3-(2-Naphthyl)-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-3-(2-Naphthyl)-L-alanine(58438-04-3)
• EPA Substance Registry System: Boc-3-(2-Naphthyl)-L-alanine(58438-04-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 58438-04-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-3-(2-Naphthyl)-L-alanine is used as a reagent for the synthesis of dipeptidyl nitriles, which are potent and reversible inhibitors of Cathepsin C. This makes it a valuable component in the development of drugs targeting proteolytic enzymes, potentially leading to treatments for various diseases and conditions.
Used in Organic Synthesis:
Boc-3-(2-Naphthyl)-L-alanine is used as a key intermediate in the synthesis of complex organic molecules, particularly those with biological activity. Its unique structure allows for the creation of novel compounds with potential applications in various fields, such as medicine, agrochemistry, and materials science.
Used in Research and Development:
Boc-3-(2-Naphthyl)-L-alanine is used as a research tool in the study of enzyme inhibition, protein structure, and other biological processes. Its ability to act as a potent and reversible inhibitor of Cathepsin C makes it a valuable probe for understanding the mechanisms of enzyme function and the development of new therapeutic agents.

InChI:InChI=1/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-12-8-9-13-6-4-5-7-14(13)10-12/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/t15-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 6960-34-5 L-3-(2-naphthyl)alanine 
• 37447-33-9 acetylamino-[2]naphthylmethyl-malonic acid diethyl ester 
• 37439-99-9 (S)-N-acetyl-3-(2-naphthyl)alanine 
• 136015-50-4 2-Acetylamino-2-naphthalen-2-ylmethyl-malonic acid monoethyl ester 
• 172214-89-0 2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 74651-77-7 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 143218-07-9 ethyl 2-acetylamino-2-cyano-3-(naphthalen-2-yl)propanoate 
• 63024-44-2 2-Amino-3-naphthalen-2-yl-propionic acid; hydrochloride 
• 636572-72-0 C₂₃H₂₉NO₆ 
• 58438-04-3 N-tert-butoxycarbonyl-3-(2-naphthyl)-alanine 
• 1393112-55-4 (S)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate 
• 1393112-51-0 (RS)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate 

Downstream Products

• 92635-09-1 [(S)-2-Naphthalen-2-yl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 251308-65-3 (S)-3-Naphthalen-2-ylmethyl-1-(3-phenyl-propyl)-piperazine-2,5-dione 
• 251308-52-8 [((S)-2-Amino-3-naphthalen-2-yl-propionyl)-(3-phenyl-propyl)-amino]-acetic acid methyl ester 
• 251308-92-6 [(S)-2-Naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetic acid 
• 251308-79-9 [2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetic acid tert-butyl ester 
• 251309-08-7 N-((S)-1-{(S)-1-[Imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-2-[(S)-2-naphthalen-2-ylmethyl-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetamide 
• 143457-42-5 N-{D,L-2-(hydroxyaminocarbonyl)methyl-4-methylpentanoyl}-L-3-(2'-naphthyl)alanyl-L-alanine Methylamide 
• 1333389-14-2 (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-3-yl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoate 
• 1333389-21-1 (S)-(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl 2-amino-3-(naphthalen-2-yl)propanoate 
• 1333389-30-2 NapLysAlaAcm 
• 1393112-51-0 (RS)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate 
• 602301-10-0 C₃₆H₄₀N₂O₇ 
• 136015-54-8 (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-2-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid 
• 109996-50-1 {(S)-1-[(S)-1-((1S,2S)-2-Hydroxy-1-isobutyl-5-methyl-hexylcarbamoyl)-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-naphthalen-2-yl-ethyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

ARYLPYRROLIDINE DICARBOXYLIC ACID AMIDE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a pyrrolidine derivative capable of catalyzing an asymmetric oxidation reaction of an alkene compound. SOLUTION: There is provided an arylpyrrolidine dicarboxylic acid amide derivative exemplified by cat.A in the following formula. There is provided an asymmetric oxidation catalyst having optical purity of 50%. There is provided a manufacturing method of an optically active epoxy compound including contacting the compound with an alkene derivative in addition to a co-oxidant. There is provided a manufacturing method of an optically active epoxy compound, in which the alkene derivative is a substituted alkene derivative having a functional group containing N or O at 3 position of a double bond. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts

We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-L-alanine amide. The asymmetric environment created by intramolecular π - cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.

Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution

A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-α-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process. In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an l-configuration almost quantitatively and with complete enantioselectivity. 2012 Elsevier Ltd.

Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds

A highly potent CXCR4 antagonist, compound 2, was previously found by using two orthogonal cyclic pentapeptide libraries involving conformation-based and sequence-based libraries based on the pharmacophore of a 14-mer peptidic antagonist, 1. Herein, cyclic tetrapeptides derived from replacements of the dipeptide unit (Nal-Gly) with a γ-amino acid and pseudopeptides cyclized by disulfide and olefin bridges were synthesized to find novel scaffold structures different from that of cyclic pentapeptides. These compounds contain a reduced number of peptide bonds compared to compound 2. Furthermore, several analogues with chemical modification of the side chain of Arg4 in 2 were also prepared. From these, several new leads possessing high to moderate CXCR4-antagonistic activity were characterized.

Substituted alkyldiamine derivatives

The present invention relates to novel substituted alkyldiamine derivatives and pharmaceutically acceptable salts thereof which are useful tachykinin antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions including asthma, cough, and bronchitis.

Cross-linked crystals of subtilisin: Versatile catalyst for organic synthesis

Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.

Tetrapeptide derivatives and analogues

The C-terminal tetrapeptide of gastrin, Trp-Met-Asp-Phe-NH 2, possesses gastrin pharmacological activity. Replacement of the methionyl moiety in the gastrin tetrapeptide, or its analogs, with a naphthylalanyl group produces compounds which interact with gastrin and/or cholecystokinin receptors, but have reduced gastrin and/or cholecystokinin agonist activity. Such partial agonists or antagonists of gastrin and/or cholecystokinin provide useful therapeutic agents.

Synthesis and biological activity of ketomethylene pseudopeptide analogues as thrombin inhibitors

Ketomethylene pseudopeptide analogues Aa-Pro-Argψ(COCH2)Gly-pip, 1, where Aa are D- or L-amino acids (Dpa, β,β-diphenylalanine; αNal, α- naphthylalanine; βNal, β-naphthylalanine; Fgl, fluorenylglycine) with highly lipophilic side chains and ψ(COCH2) is a ketomethylene pseudopeptide bond, have been synthesized through a modified Dakin-West reaction under very mild conditions with a high yield using tripeptide 4 with a labile functional group directly on the side chain. Their enzymatic assay of thrombin inhibition has been carried out. The structure-activity relationship study indicated that a lipophilic side chain on the amino acid in the P3 position is very important for binding to the apolar site of thrombin. Compound 1a with D-Dpa at the P3 position has a K(i) of 0.2 μM and it doubles thrombin clotting time at only 3 times higher concentration. These values are about 7 times better than those of the corresponding D-Phe analogues. Furthermore, 1a shows poor inhibitory activity against plasmin, factor Xa, urokinase, and kallikrein. Preliminary in vivo testing (3-4-kg rabbit as the animal model) shows no observable side effect (change of blood pressure and accumulation of blood platelet in lungs) at a dose of 1 mg/kg.

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.