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Application Area

N-α-Acetyl-D-alanyl-D-lactic acid

* 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-005923

CAS number

136577-05-4

Molecular Formula

C8H13NO5

Molecular Weight

203.19

IUPAC Name

(2R)-2-[(2R)-2-acetamidopropanoyl]oxypropanoic acid

Synonyms

Ac-D-Ala-D-lactic acid

Storage

Store at -20°C

InChI

InChI=1S/C8H13NO5/c1-4(9-6(3)10)8(13)14-5(2)7(11)12/h4-5H,1-3H3,(H,9,10)(H,11,12)/t4-,5-/m1/s1

InChI Key

FIQRMBHOTDMNOQ-RFZPGFLSSA-N

Canonical SMILES

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

N-α-Acetyl-D-alanyl-D-lactic acid, a versatile biochemical compound, finds diverse applications in bioscience research and medicine. Here are the key applications of N-α-Acetyl-D-alanyl-D-lactic acid presented with high perplexity and burstiness:

Antibiotic Resistance Studies: Delving into the realm of gram-positive bacteria, particularly in the context of vancomycin resistance, researchers harness N-α-Acetyl-D-alanyl-D-lactic acid to probe the intricate mechanisms at play. By integrating this compound into bacterial peptidoglycan, scientists unravel how bacteria manipulate their cell wall architecture to evade antibiotic interactions. This knowledge is paramount in formulating innovative strategies to combat the emergence of antibiotic-resistant bacterial strains.

Biochemical Pathway Elucidation: Offering invaluable insights into biosynthetic pathways involving peptidoglycan precursors, N-α-Acetyl-D-alanyl-D-lactic acid serves as a crucial tool. Researchers leverage this compound to track the incorporation and utilization of modified amino acids in bacterial cell wall synthesis. These investigations aid in pinpointing key enzyme targets and critical steps essential for bacterial growth and survival, shedding light on the intricate web of biochemical processes.

Drug Development: Pioneering a new era in pharmacology, N-α-Acetyl-D-alanyl-D-lactic acid plays a pivotal role in the development of next-generation antibiotics tailored to combat resistant bacterial strains. By scrutinizing the interactions of this compound with potential drug candidates, researchers craft more potent and targeted treatment solutions. This innovative approach addresses the pressing public health challenge posed by the rise of multidrug-resistant bacterial infections, offering hope for improved therapeutic outcomes.

Structural Biology: Unveiling the complex interplay between antibiotics and bacterial cell walls, N-α-Acetyl-D-alanyl-D-lactic acid is a cornerstone in structural biology research. Scientists employ sophisticated imaging techniques, including crystallography, to visualize how this compound modulates the binding sites of antibiotics like vancomycin. These profound insights drive rational drug design efforts and enhance the efficacy of existing antibiotic therapies, propelling advancements in the fight against infectious diseases.

1. Free lactic acid production under acidic conditions by lactic acid bacteria strains: challenges and future prospects

Mamata Singhvi, Takeshi Zendo, Kenji Sonomoto Appl Microbiol Biotechnol. 2018 Jul;102(14):5911-5924. doi: 10.1007/s00253-018-9092-4. Epub 2018 May 26.

Lactic acid (LA) is an important platform chemical due to its significant applications in various fields and its use as a monomer for the production of biodegradable poly(lactic acid) (PLA). Free LA production is required to get rid of CaSO4, a waste material produced during fermentation at neutral pH which will lead to easy purification of LA required for the production of biodegradable PLA. Additionally, there is no need to use corrosive acids to release free LA from the calcium lactate produced during neutral fermentation. To date, several attempts have been made to improve the acid tolerance of lactic acid bacteria (LAB) by using both genome-shuffling approaches and rational design based on known mechanisms of LA tolerance and gene deletion in yeast strains. However, the lack of knowledge and the complexity of acid-tolerance mechanisms have made it challenging to generate LA-tolerant strains by simply modifying few target genes. Currently, adaptive evolution has proven an efficient strategy to improve the LA tolerance of individual/engineered strains. The main objectives of this article are to summarize the conventional biotechnological LA fermentation processes to date, assess their overall economic and environmental cost, and to introduce modern LA fermentation strategies for free LA production. In this review, we provide a broad overview of free LA fermentation processes using robust LAB that can ferment in acidic environments, the obstacles to these processes and their possible solutions, and the impact on future development of free LA fermentation processes commercially.

2. The Stephan Curve revisited

William H Bowen Odontology. 2013 Jan;101(1):2-8. doi: 10.1007/s10266-012-0092-z. Epub 2012 Dec 6.

The Stephan Curve has played a dominant role in caries research over the past several decades. What is so remarkable about the Stephan Curve is the plethora of interactions it illustrates and yet acid production remains the dominant focus. Using sophisticated technology, it is possible to measure pH changes in plaque; however, these observations may carry a false sense of accuracy. Recent observations have shown that there may be multiple pH values within the plaque matrix, thus emphasizing the importance of the milieu within which acid is formed. Although acid production is indeed the immediate proximate cause of tooth dissolution, the influence of alkali production within plaque has received relative scant attention. Excessive reliance on Stephan Curve leads to describing foods as "safe" if they do not lower the pH below the so-called "critical pH" at which point it is postulated enamel dissolves. Acid production is just one of many biological processes that occur within plaque when exposed to sugar. Exploration of methods to enhance alkali production could produce rich research dividends.

3. Acidity characterization of heterogeneous catalysts by solid-state NMR spectroscopy using probe molecules

Anmin Zheng, Shang-Bin Liu, Feng Deng Solid State Nucl Magn Reson. 2013 Oct-Nov;55-56:12-27. doi: 10.1016/j.ssnmr.2013.09.001. Epub 2013 Sep 20.

Characterization of the surface acidic properties of solid acid catalysts is a key issue in heterogeneous catalysis. Important acid features of solid acids, such as their type (Brønsted vs. Lewis acid), distribution and accessibility (internal vs. external sites), concentration (amount), and strength of acid sites are crucial factors dictating their reactivity and selectivity. This short review provides information on different solid-state NMR techniques used for acidity characterization of solid acid catalysts. In particular, different approaches using probe molecules containing a specific nucleus of interest, such as pyridine-d5, 2-(13)C-acetone, trimethylphosphine, and trimethylphosphine oxide, are compared. Incorporation of valuable information (such as the adsorption structure, deprotonation energy, and NMR parameters) from density functional theory (DFT) calculations can yield explicit correlations between the chemical shift of adsorbed probe molecules and the intrinsic acid strength of solid acids. Methods that combine experimental NMR data with DFT calculations can therefore provide both qualitative and quantitative information on acid sites.