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Application Area

Acetyl-DL-alanine

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

Category

DL-Amino Acids

Catalog number

BAT-003572

CAS number

1115-69-1

Molecular Formula

C5H9NO3

Molecular Weight

131.10

IUPAC Name

2-acetamidopropanoic acid

Synonyms

Ac-DL-Ala-OH; 2-acetamidopropanoic acid

Appearance

White to off-white powder

Purity

≥ 98% (HPLC)

Density

1.170±0.06 g/cm3(Predicted)

Melting Point

137-139 °C

Boiling Point

369.7±25.0 °C(Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)

InChI Key

KTHDTJVBEPMMGL-UHFFFAOYSA-N

Canonical SMILES

CC(C(=O)O)NC(=O)C

Acetyl-DL-alanine, an amino acid derivative widely used across scientific and industrial domains, showcases a diverse range of applications. Here are the key applications of Acetyl-DL-alanine, presented with a high degree of perplexity and burstiness:

Pharmaceutical Synthesis: Playing a crucial role as an intermediate in pharmaceutical synthesis, Acetyl-DL-alanine contributes to the creation of various pharmacological compounds. Its exceptional properties allow for integration into drugs designed to target specific metabolic pathways, thereby facilitating the development of medications with enhanced efficacy and precise targeted actions.

Biochemical Research: Within the realm of biochemical research, Acetyl-DL-alanine serves as a vital tool for investigating enzyme activities and metabolic pathways. Researchers utilize this compound to explore the intricate interactions between enzymes and substrates, shedding light on how these interactions influence cellular metabolism at a holistic level. This knowledge is essential for unraveling the complexities of fundamental biological processes and advancing enzyme-related technologies.

Nutritional Supplements: Widely embraced in the realm of nutritional supplements, Acetyl-DL-alanine is a favored ingredient in products geared towards augmenting athletic performance and accelerating recovery. Believed to bolster protein synthesis and muscle rejuvenation, this compound enjoys popularity among athletes and bodybuilders alike. By offering a readily absorbable form of alanine, a pivotal amino acid for muscle metabolism, Acetyl-DL-alanine continues to support individuals striving for peak physical performance.

Industrial Biotechnology: Embraced for its versatile applications in industrial biotechnology, Acetyl-DL-alanine acts as a foundational component for the production of biodegradable polymers and specialty chemicals. Its integration into polymer structures elevates material properties, such as biodegradability and mechanical resilience, thus driving the development of environmentally sustainable materials with enhanced performance characteristics. This underscores the pivotal role of Acetyl-DL-alanine in spearheading innovations within the realm of industrial biotechnology.

1. Coupling of alanine racemase and D-alanine dehydrogenase to active transport of amino acids in Escherichia coli B membrane vesicles

G Kaczorowski, L Shaw, M F-entes, C Walsh J Biol Chem. 1975 Apr 25;250(8):2855-65.

Isolated membrane vesicles from Escherichia coli B grown on DL-alanine-glycerol carry out amino acid active transport coupled to D-alanine oxidation by a membrane-bound dehydrogenase. Several other D-amino acids are substrates for this D-alanine dehydrogenase and also drive concentrative uptake of solutes. Additionally, L-alanine and L-serine can energize solute transport by virtue of conversion to oxidizable D isomers by a membrane-bound alanine racemase. No other physiological L-amino acids were effective. Both membrane enzymes and consequent solute transport are markedly reduced in vesicles from glucose-grown cells. Respiratory chain uncouplers abolish the racemase-dehydrogenase-supported transport activity. When amino-oxyacetate at 10-4 M is added to the vesicles, the racemase activity and transport driven by L-alanine and L-serine is specifically and reversibly inhibited. D-Alanine-driven transport is unaffected. Similarly beta-chloro-L-alanine is an irreversible inactivator of the bound racemase but not the D-alanine dehydrogenase. Both the D and L isomers of beta-chloroalanine support oxygen uptake by the vesicles and initially stimulate L-(14C)proline active transport. However, oxidation of the beta-chloro-D-alanine rapidly uncouples active transport from substrate oxidation. This transport inactivation can be protected partially by dithiothreitol, putatively scavenging a reactive product of chloroalanine oxidation. Authentic beta-chloropyruvate produces the same transport uncoupling. When beta-chloro-L-alanine is employed as a substrate, no such transport inactivation is observed. This difference may stem from the possibility that the alanine racemase eliminates HCl from beta-chloro-L-alanine producing pyruvate, not the beta-chloropyruvate that would arise from racemization and then dehydrogenation. We have shown that exogenous pyruvate is oxidized by the vesicles and will also stimulate active transport of amino acids.

2. Enzymatic transformations of 3-chloroalanine into useful amino acids

T Nagasawa, H Yamada Appl Biochem Biotechnol. 1986 Oct;13(2):147-65. doi: 10.1007/BF02798908.

The investigation of the combination of enzymatic and chemical synthetic processes for the production of useful compounds has been carried out. This review focuses on the enzymatic transformation of chemically synthesized 3-chloroalanine into useful amino acids.