Z-D-aspartic acid
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Z-D-aspartic acid

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Category
CBZ-Amino Acids
Catalog number
BAT-003281
CAS number
78663-07-7
Molecular Formula
C12H13NO6
Molecular Weight
267.20
Z-D-aspartic acid
IUPAC Name
(2R)-2-(phenylmethoxycarbonylamino)butanedioic acid
Synonyms
Z-D-Asp-OH; (R)-2-(((Benzyloxy)Carbonyl)Amino)Succinic Acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.404±0.06 g/cm3(Predicted)
Melting Point
110-116 °C
Boiling Point
472.8±45.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H13NO6/c14-10(15)6-9(11(16)17)13-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,18)(H,14,15)(H,16,17)/t9-/m1/s1
InChI Key
XYXYXSKSTZAEJW-SECBINFHSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CC(=O)O)C(=O)O

Z-D-aspartic acid, a chiral variant of aspartic acid, boasts a multitude of applications in bioscience and biotechnology. Here are four pivotal applications:

Pharmaceutical Research: Delving into pharmaceutical research, Z-D-aspartic acid emerges as a key player in exploring its therapeutic potential. It contributes to the synthesis of peptide-based drugs envisioned for combating diverse diseases. Understanding its pharmacokinetics and dynamics serves as a linchpin in crafting more potent and precisely targeted medications with enhanced efficacy.

Neurobiology Studies: Within the domain of neurobiology, Z-D-aspartic acid grips the attention for its pivotal role in neurotransmitter synthesis and neural functionality. Researchers scrutinize its impact on neural cells to unearth potential therapeutic avenues for neurodegenerative afflictions like Alzheimer's and Parkinson's. Its distinctive attributes offer a window into modulating synaptic activity and neural adaptability, unraveling the complexities of neural regulation.

Enzyme Engineering: Harnessing Z-D-aspartic acid in enzyme engineering unfolds vistas of creating asymmetric catalysts for chemical syntheses. By integrating this chiral amino acid, scientists pave the way for crafting catalysts that steer towards the synthesis of enantiomerically pure compounds. This breakthrough holds profound implications in the pharmaceutical and chemical sectors, augmenting the efficiency and selectivity of diverse reactions.

Nutritional Biochemistry: Diving into the depths of nutritional biochemistry, the exploration of Z-D-aspartic acid uncovers its potential benefits and metabolic effects. Studies delve into its role in protein biosynthesis, energy generation, and overall amino acid metabolism, shedding light on its nutritional virtues. Unraveling its nutritional nuances may pave the path for developing dietary supplements aimed at fortifying metabolic well-being, heralding a new age of metabolic support through advanced nutritional interventions.

1. 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.
2. Physiological Genomics of the Highly Weak-Acid-Tolerant Food Spoilage Yeasts of Zygosaccharomyces bailii sensu lato
Margarida Palma, Isabel Sá-Correia Prog Mol Subcell Biol. 2019;58:85-109. doi: 10.1007/978-3-030-13035-0_4.
Zygosaccharomyces bailii and two closely related species, Z. parabailii and Z. pseudobailii ("Z. bailii species complex", "Z. bailii sensu lato" or simply "Z. bailii (s.l.)"), are frequently implicated in the spoilage of acidified preserved foods and beverages due to their tolerance to very high concentrations of weak acids used as food preservatives. The recent sequencing and annotation of these species' genomes have clarified their genomic organization and phylogenetic relationship, which includes events of interspecies hybridization. Mechanistic insights into their adaptation and tolerance to weak acids (e.g., acetic and lactic acids) are also being revealed. Moreover, the potential of Z. bailii (s.l.) to be used in industrial biotechnological processes as interesting cell factories for the production of organic acids, reduction of the ethanol content, increase of alcoholic beverages aroma complexity, as well as of genetic source for increasing weak acid resistance in yeast, is currently being considered. This chapter includes taxonomical, ecological, physiological, and biochemical aspects of Z. bailii (s.l.). The focus is on the exploitation of physiological genomics approaches that are providing the indispensable holistic knowledge to guide the effective design of strategies to overcome food spoilage or the rational exploitation of these yeasts as promising cell factories.
3. 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.
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