Fmoc-L-aspartic acid
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Fmoc-L-aspartic acid

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N-Fmoc-L-aspartic acid is an N-Fmoc-protected form of L-Aspartic acid. L-Aspartic acid is a non-essential amino acid that is used to biosynthesize other amino acids within the human body. L-Aspartic acid also increases membrane conductance of mammalian neurons by voltage-dependent means, causing depolarization and nerve impulses that travel to key areas of the central nervous system.

Category
Fmoc-Amino Acids
Catalog number
BAT-003732
CAS number
119062-05-4
Molecular Formula
C19H17NO6
Molecular Weight
355.35
Fmoc-L-aspartic acid
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioic acid
Synonyms
Fmoc-L-Asp-OH; Fmoc-Asp-OH; N-Fmoc-L-aspartic acid; N-[(9H-Fluoren-9-ylMethoxy)carbonyl]-L-aspartic Acid; Fmoc-L-aspartic acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.399±0.06 g/cm3
Melting Point
186-192 °C
Boiling Point
587.2±45.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C19H17NO6/c21-17(22)9-16(18(23)24)20-19(25)26-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H,20,25)(H,21,22)(H,23,24)/t16-/m0/s1
InChI Key
KSDTXRUIZMTBNV-INIZCTEOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(=O)O)C(=O)O

Fmoc-L-aspartic acid, a derivative of aspartic acid extensively utilized in peptide synthesis and biochemical research, offers a plethora of applications. Here are four key applications of Fmoc-L-aspartic acid presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in solid-phase peptide synthesis, Fmoc-L-aspartic acid plays a pivotal role in constructing peptides. Its Fmoc protective group ensures precise deprotection and efficient chain elongation, enabling researchers to craft peptides for investigating diverse realms like protein-protein interactions, enzyme functionalities, and therapeutic potentials with meticulous detail and nuance.

Protein Engineering: Scientists harness the power of Fmoc-L-aspartic acid to introduce aspartic acid residues with surgical precision into proteins, allowing for in-depth exploration of how modifications at specific locations influence protein structure, stability, and function. These engineered proteins serve as invaluable tools for unraveling intricate biological processes and designing novel biotherapeutic agents with groundbreaking implications.

Drug Discovery: In the realm of drug discovery, Fmoc-L-aspartic acid emerges as a crucial component in designing and synthesizing peptide-based drug candidates tailored for exceptional affinity and specificity towards target molecules, such as receptors or enzymes. This tailored approach holds immense promise in developing inhibitors or modulators for treating conditions like cancer and autoimmune disorders.

Bioconjugation: Employed in sophisticated bioconjugation techniques, Fmoc-L-aspartic acid facilitates the linking of peptides to diverse biomolecules like fluorescent dyes or polymers, essential for applications spanning imaging, diagnostics, and targeted drug delivery. The conjugated peptides serve as potent tools for visualizing intricate cellular processes and delivering therapeutic agents directly to afflicted cells, opening up new horizons in personalized medicine and precision-targeted therapies.

1. 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.
2. 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.
3. Dietary Acid Load Associated with Hypertension and Diabetes in the Elderly
Tulay Omma, Nese Ersoz Gulcelik, Fatmanur Humeyra Zengin, Irfan Karahan, Cavit Culha Curr Aging Sci. 2022 Aug 4;15(3):242-251. doi: 10.2174/1874609815666220328123744.
Background: Diet can affect the body's acid-base balance due to its content of acid or base precursors. There is conflicting evidence for the role of metabolic acidosis in the development of cardiometabolic disorders, hypertension (HT), and insulin resistance (IR). Objective: We hypothesized that dietary acid load (DAL) is associated with adverse metabolic risk factors and aimed to investigate this in the elderly. Methods: A total of 114 elderly participants were included in the study. The participants were divided into four groups, such as HT, diabetes (DM), both HT and DM, and healthy controls. Anthropometric, biochemical, and clinical findings were recorded. Potential renal acid load (PRAL) and net endogenous acid production (NEAP) results were obtained for three days, 24-hour dietary records via a nutrient database program (BeBiS software program). Results: The groups were matched for age, gender, and BMI. There was a statistically significant difference between the groups regarding NEAP (p =0.01) and no significant difference for PRAL ( p = 0.086). The lowest NEAP and PRAL levels were seen in the control group while the highest in the HT group. Both NEAP and PRAL were correlated with waist circumference (r = 0,325, p = 0.001; r=0,231, p =0,016, respectively). Conclusion: Our data confirmed that subjects with HT and DM had diets with greater acid-forming potential. High NEAP may be a risk factor for chronic metabolic diseases, particularly HT. PRAL could not be shown as a significantly different marker in all participants. Dietary content has a significant contribution to the reduction of cardiovascular risk factors, such as HT, DM, and obesity.
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