D-Alanine β-naphthylamide hydrochloride
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D-Alanine β-naphthylamide hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-003525
CAS number
201984-32-9
Molecular Formula
C13H14N2O·HCl
Molecular Weight
250.73
D-Alanine β-naphthylamide hydrochloride
IUPAC Name
(2R)-2-amino-N-naphthalen-2-ylpropanamide;hydrochloride
Synonyms
D-Ala-βNA HCl; (R)-2-Amino-N-(naphthalen-2-yl)propanamide hydrochloride
Storage
Store at 2-8°C
InChI
InChI=1S/C13H14N2O.ClH/c1-9(14)13(16)15-12-7-6-10-4-2-3-5-11(10)8-12;/h2-9H,14H2,1H3,(H,15,16);1H/t9-;/m1./s1
InChI Key
WNLRRMRLNYQNOZ-SBSPUUFOSA-N
Canonical SMILES
CC(C(=O)NC1=CC2=CC=CC=C2C=C1)N.Cl

D-Alanine β-naphthylamide hydrochloride is a synthetic compound used primarily in microbiological and biochemical applications. Here are some key applications of D-Alanine β-naphthylamide hydrochloride:

Microbial Enzyme Activity Assays: This compound is used to identify and quantify enzymatic activity, particularly of D-amino acid-specific enzymes like D-alanine aminopeptidases in bacterial cells. When bacterial cultures are treated with D-Alanine β-naphthylamide hydrochloride, the enzymatic breakdown releases β-naphthylamide, which can be detected spectrophotometrically. This helps in the identification of bacterial species and understanding their enzymatic profiles.

Microbial Classification: D-Alanine β-naphthylamide hydrochloride is employed in microbiology for the classification and differentiation of bacterial strains. Certain bacteria can hydrolyze this substrate to produce a chromogenic reaction that is easily observable. This property is useful in diagnostic microbiology for rapid and specific bacterial identification.

Antimicrobial Susceptibility Testing: In antimicrobial research, this compound serves as a substrate for evaluating the susceptibility of bacteria to antibiotics. The reductions in enzymatic hydrolysis of D-Alanine β-naphthylamide hydrochloride in the presence of antibiotics can indicate the effectiveness of the antimicrobial agents. This contributes to the development and optimization of new antibacterial therapies.

Cell Wall Biosynthesis Studies: D-Alanine β-naphthylamide hydrochloride is used in studies investigating bacterial cell wall biosynthesis. Since D-alanine is a critical component in peptidoglycan cross-linking within bacterial cell walls, its analogs like D-Alanine β-naphthylamide hydrochloride can be used to explore the pathways and enzymes involved. This knowledge is crucial for discovering novel targets for antibacterial drug development.

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