76985-09-6

Basic information

• Product Name: 3-(2-Naphthyl)-D-alanine
• Synonyms: RARECHEM BK PT 0100;(R)-ALPHA-AMINO-2-NAPHTHALENEPROPIONIC ACID;(R)-2-AMINO-3-(NAPHTHALEN-2-YL)PROPANOIC ACID HYDROCHLORIDE;(R)-2-AMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID;H-D-NAL(2)-OH;H-D-2-NAL-OH;H-D-ALA(2-NAPHTHYL)-OH;H-D-ALA(2-NAPH)-OH
• CAS NO: 76985-09-6
• Molecular Formula: C₁₃H₁₃NO₂
• Molecular Weight: 215.25
• Product Categories: Pharmaceutical Raw Materials;Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Alanine [Ala, A];Unusual Amino Acids;AlanineAmino Acids;Amino Acid Derivatives;Alanine DerivativesAmino Acids;I - Z;Modified Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives;a-amino;wq
• Mol File: 76985-09-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 355.53°C (rough estimate)
• Flash Point: 203.2 °C
• Appearance: Off-white/Solid
• Density: 1.1242 (rough estimate)
• Vapor Pressure: 1.54E-07mmHg at 25°C
• Refractive Index: 13 ° (C=1, 1mol/L HCl)
• Storage Temp.: 2-8°C
• PKA: 2.21±0.30(Predicted)
• CAS DataBase Reference: 3-(2-Naphthyl)-D-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Naphthyl)-D-alanine(76985-09-6)
• EPA Substance Registry System: 3-(2-Naphthyl)-D-alanine(76985-09-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 76985-09-6(Hazardous Substances Data)

Usage

Chemical Properties

white fine powder

InChI:InChI=1/C13H13NO2/c14-12(13(15)16)8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7,12H,8,14H2,(H,15,16)/t12-/m1/s1

Upstream product

• 109063-69-6 (S)-methyl 2-amino-3-(naphthalen-2-yl)propanoate 
• 14108-60-2 2-amino-3-(2-naphthyl)propanoic acid 
• 111726-64-8 3-(naphthalene-2-yl)-2-oxopropanoic acid 
• 136015-51-5 (R)-2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 
• 56-40-6 glycine 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 7732-18-5 water 
• 35939-28-7 (S)-N-acetyl-3-(2-naphthyl)alanine methyl ester 
• 35799-85-0 (R)-N-Acetyl-3-(2-naphthyl)alanine Methyl Ester 
• 37439-99-9 (RS)-N-acetyl-2-naphthylalanine 
• 603944-76-9 (±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate 
• 172214-89-0 2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 
• 37447-33-9 acetylamino-[2]naphthylmethyl-malonic acid diethyl ester 
• 103774-97-6 N-(trifluoroacetyl)-3-(2-naphthyl)-D-alanine 

Downstream Products

• 63024-26-0 methyl (S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride 
• 240428-63-1 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-(2-naphthalenyl)-D-alanine 
• 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 
• 136794-01-9 (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-2-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid benzyl ester 
• 219496-44-3 Benzyl (S)-2-amino-3-(2-naphthyl) propionate tosylate 
• 56583-58-5 N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine 
• 76985-10-9 Boc-D-2Nal-OH 
• 105426-00-4 N-benzyloxycarbonyl-L-naphthylalanyl-L-naphthylalanine methyl ester 
• 202811-56-1 (2R)-2-(2-naphthyl)methyl-3-oxo-4-phenethylpiperazine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Drug Design Inspired by Nature: Crystallographic Detection of an Auto-Tailored Protease Inhibitor Template

De novo drug discovery is still a challenge in the search for potent and selective modulators of therapeutically relevant target proteins. Here, we disclose the unexpected discovery of a peptidic ligand 1 by X-ray crystallography, which was auto-tailored by the therapeutic target MMP-13 through partial self-degradation and subsequent structure-based optimization to a highly potent and selective β-sheet peptidomimetic inhibitor derived from the endogenous tissue inhibitors of metalloproteinases (TIMPs). The incorporation of non-proteinogenic amino acids in combination with a cyclization strategy proved to be key for the de novo design of TIMP peptidomimetics. The optimized cyclic peptide 4 (ZHAWOC7726) is membrane permeable with an IC50 of 21 nm for MMP-13 and an attractive selectivity profile with respect to a polypharmacology approach including the anticancer targets MMP-2 (IC50: 170 nm) and MMP-9 (IC50: 140 nm).

Asymmetric Transamination of α-Keto Acids Catalyzed by Chiral Pyridoxamines

A new type of novel chiral pyridoxamines 3a-g containing a side chain has been developed. The pyridoxamines displayed catalytic activity and promising enantioselectivity in biomimetic asymmetric transamination of α-keto acids, to give various α-amino acids in 47-90% yields with up to 87% ee's under very mild conditions. An interesting effect of the side chain on enantioselectivity was observed in the reaction.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.