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Application Area

D-Alanine amide hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

D-Amino Acids

Catalog number

BAT-003532

CAS number

71810-97-4

Molecular Formula

C3H8N2O·HCl

Molecular Weight

124.60

IUPAC Name

(2R)-2-aminopropanamide;hydrochloride

Synonyms

D-Ala-NH2 HCl; (2R)-2-aminopropanamide hydrochloride

Purity

≥ 99% (HPLC)

Melting Point

208-215 °C

Boiling Point

247.4°C at 760 mmHg

Storage

Store at 2-8°C

InChI

InChI=1S/C3H8N2O.ClH/c1-2(4)3(5)6;/h2H,4H2,1H3,(H2,5,6);1H/t2-;/m1./s1

InChI Key

FIAINKIUSZGVGX-HSHFZTNMSA-N

Canonical SMILES

CC(C(=O)N)N.Cl

D-Alanine amide hydrochloride, a chemical compound with diverse applications in the biochemical and pharmaceutical domains, is a versatile tool for various scientific endeavors. Here are the key applications, presented with heightened perplexity and burstiness:

Nutritional Research: Delving into the realms of nutrition and metabolism, D-Alanine amide hydrochloride plays a pivotal role in research investigations exploring the intricate roles of amino acids. Serving as a model compound, it serves to unravel how amino acid derivatives impact cellular growth and nutrient uptake, shedding light on metabolic fluxes and nutritional exigencies across a spectrum of organisms.

Pharmaceutical Synthesis: Positioned at the nexus of pharmaceutical innovation, D-Alanine amide hydrochloride emerges as a critical intermediate in synthesizing an array of pharmaceutical compounds, especially in the realm of peptide-based drug development. Enhancing the stability and bioactivity of therapeutic peptides, this compound serves as the linchpin for crafting medications with enhanced therapeutic efficacy and bioavailability.

Microbial Culture: Within the domain of microbiology, D-Alanine amide hydrochloride assumes a pivotal role as a selective agent in microbial culture media. Facilitating the growth of specific bacterial strains while impeding others, this compound aids in discerning and studying particular microbes, thereby enriching the landscape of microbiological research and industrial microbiology processes.

Enzymatic Studies: Embarking on a journey into the intricate workings of enzymes, D-Alanine amide hydrochloride emerges as a crucial tool for investigating the functions and mechanisms of enzymes interacting with amino acid derivatives. Acting as a substrate or inhibitor, this compound unravels the nuances of enzyme kinetics and catalytic pathways, serving as a cornerstone for understanding enzyme dynamics and steering the development of enzyme-centric industrial applications.

1. Imitation-mussel fluorescent silicon quantum dots for selective labeling and imaging of bacteria and biofilms

Jiayi Lin, Linlin Xu, Yuling Zheng, Dalin Wu, Jun Yue Front Bioeng Biotechnol. 2022 Aug 12;10:971682. doi: 10.3389/fbioe.2022.971682. eCollection 2022.

Selective labeling of distinct bacteria and biofilm is poised for the fundamental understanding of bacterial activities, interactions, and coupled phenomena occurring at the microscale. However, a simple and effective way to achieve selective bacterial labeling is still lacking. Herein, we report a fluorescence probe with core-shell nanostructure that has polydopamine (PDA) coating on the surface of fluorescent silicon quantum dots (SiQDs@PDA). The surface of the SiQDs@PDA can be functionalized by various molecules (2-mercaptoethylamine hydrochloride, PEG, d-alanine, glucose amide) through different strategies (Michael addition, π-π interaction, and ion-ion interaction). Importantly, the d-alanine (D-Ala)- and gluconamide (Glc)-functionalized SiQDs@PDA fluorescence probes are capable of selectively labeling gram-positive and gram-negative bacteria, as well as their biofilms. The excellent performance in universal functionalization and selective labeling and imaging of bacteria and their biofilms demonstrate that SiQDs@PDA are a promising fluorescence tool in microbe research.

2. Antinociception produced by oral, subcutaneous or intrathecal administration of SC-39566, an opioid dipeptide arylalkylamide, in the rodent

D L Hammond, A Stapelfeld, E J Drower, M A Savage, L Tam, R H Mazur J Pharmacol Exp Ther. 1994 Feb;268(2):607-15.

This study characterized the prototypic "minimum structure" enkephalin SC-39566 [2,6-dimethyl-L-tyrosinyl-D-alanine-(3-phenyl-1-propyl)-amide hydrochloride]. SC-39566 bound with highest affinity to mu opioid receptors (Ki, 0.13 nM), as well as to delta (Ki, 4.0 nM) opioid receptors in the rat brain, and with much lower affinity to kappa opioid receptors (Ki, 83.8 nM) in the guinea pig brain. In the mouse, SC-39566 inhibited phenylbenzoquinone-induced writhing and increased tail-flick and hot-plate latencies in a dose-dependent manner after either s.c. or p.o. (i.g.; intragastrical) administration. This antinociception was antagonized by the opioid antagonist naloxone, but not by alpha adrenergic, serotonergic, histaminergic, muscarinic cholinergic or dopaminergic receptor antagonists. In the rat, SC-39566 dose-dependently inhibited acetic-acid-induced writhing after s.c. or i.g. administration and increased response latencies in the tail-flick and hot-plate test after s.c. or intrathecal (i.t.) administration. The increase in tail-flick latency produced by s.c. SC-39566 in the rat was antagonized by s.c. naloxone with an apparent pA2 value of 7.9. Pretreatment with naltrindole, a delta opioid receptor antagonist, increased the ED50 of SC-39566 by only 1.7-fold. In addition, the increase in tail-flick latency produced by i.t. SC-39566 was not antagonized by i.t. administration of naltrindole or nor-binaltorphimine, a kappa receptor antagonist. These data suggest that the antinociceptive activity of SC-39566 is mediated predominantly by mu opioid receptors.(ABSTRACT TRUNCATED AT 250 WORDS)

3. Memory of chirality of tertiary aromatic amide: application to the asymmetric synthesis of (S)-α-methylDOPA

Thi Thoa Mai, Baby Viswambharan, Didier Gori, Cyrille Kouklovsky, Valérie Alezra J Org Chem. 2012 Oct 5;77(19):8797-801. doi: 10.1021/jo301588t. Epub 2012 Sep 14.

We describe an original asymmetric synthesis of (S)-α-methylDOPA proceeding by the concept of memory of chirality, the only source of chirality being the starting D-alanine. The initial chirality of the amino acid is temporarily transferred to a dynamic axial chirality of a tertiary aromatic amide. The (S)-α-methylDOPA hydrochloride is obtained after four steps with 98% ee.