Boc-L-aspartic acid
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Boc-L-aspartic acid

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Category
BOC-Amino Acids
Catalog number
BAT-002752
CAS number
13726-67-5
Molecular Formula
C9H15NO6
Molecular Weight
233.20
Boc-L-aspartic acid
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioic acid
Synonyms
Boc-L-Asp-OH; N-(tert-Butoxycarbonyl)-L-aspartic acid
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.3397 g/cm3(rough estimate)
Melting Point
111-114 °C
Boiling Point
375.46°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H15NO6/c1-9(2,3)16-8(15)10-5(7(13)14)4-6(11)12/h5H,4H2,1-3H3,(H,10,15)(H,11,12)(H,13,14)/t5-/m0/s1
InChI Key
KAJBMCZQVSQJDE-YFKPBYRVSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)O)C(=O)O

Boc-L-aspartic acid, a versatile chemical compound, finds extensive application in peptide synthesis and various biochemical processes. Explore its multifaceted uses, presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a pivotal component in peptide and protein synthesis, Boc-L-aspartic acid plays a vital role in solid-phase peptide synthesis (SPPS). The Boc group acts as a safeguard, preventing undesired reactions and enabling precise assembly of peptides through controlled addition of amino acids in a predetermined sequence.

Pharmaceutical Development: Within the realm of drug discovery, derivatives of Boc-L-aspartic acid are instrumental in formulating peptide-based therapeutics. These peptides mimic natural signaling molecules or hormones and can be tailored to target specific receptors within the body. The Boc group ensures synthesis stability and can be selectively removed under acidic conditions, yielding the active therapeutic peptide.

Protein Engineering: Delving deeper into protein manipulation, Boc-L-aspartic acid plays a critical role in the realm of protein engineering. By integrating this compound at specific sites within proteins, researchers can delve into the function of aspartic acid residues in protein folding, stability, and activity. This understanding is pivotal for unraveling protein mechanisms and crafting engineered proteins with desired attributes.

Bioconjugation: The application of Boc-L-aspartic acid extends to bioconjugation techniques, which involve linking peptides to various molecules such as drugs, fluorescent probes, or nanoparticles. This process enhances the delivery and targeting of therapeutics, diagnostic agents, and research instruments. The Boc protective group facilitates precise modifications at specific locations within peptides or proteins, fostering tailored bioconjugation strategies.

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. 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. 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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