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Application Area

Boc-L-pyroglutamic acid

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

Category

BOC-Amino Acids

Catalog number

BAT-007120

CAS number

53100-44-0

Molecular Formula

C10H15NO5

Molecular Weight

229.23

IUPAC Name

(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-5-oxopyrrolidine-2-carboxylic acid

Synonyms

Boc-L-Pyr-OH; Boc L Pyr OH

Related CAS

4677-75-2 (dicyclohexylammonium salt)

Appearance

White to off-white powder

Purity

≥ 99% (HPLC)

Density

1.304 g/cm3

Melting Point

109-115 °C

Boiling Point

425.8°C at 760 mmHg

Storage

Store at 2-8 °C

InChI

InChI=1S/C10H15NO5/c1-10(2,3)16-9(15)11-6(8(13)14)4-5-7(11)12/h6H,4-5H2,1-3H3,(H,13,14)/t6-/m0/s1

InChI Key

MJLQPFJGZTYCMH-LURJTMIESA-N

Canonical SMILES

CC(C)(C)OC(=O)N1C(CCC1=O)C(=O)O

Boc-L-pyroglutamic acid is a derivative of pyroglutamic acid, in which the amino group is protected by a tert-butyloxycarbonyl (Boc) group. Pyroglutamic acid itself is a cyclic amino acid that plays a crucial role in the structure of various peptides and proteins. The Boc protection group allows for selective deprotection under mild conditions, making it a useful intermediate in peptide synthesis and other biochemical applications. This compound is widely used in organic chemistry, drug development, and peptide research.

One key application of Boc-L-pyroglutamic acid is in solid-phase peptide synthesis (SPPS). The Boc group serves as a protective group for the amino functionality, which can be selectively removed during peptide elongation. The stability and ease of removal of the Boc group make it an ideal choice for constructing peptides that contain pyroglutamic acid residues, which are often found in bioactive peptides and proteins. This enables the synthesis of high-purity peptides for research and therapeutic purposes.

In the field of pharmaceutical research, Boc-L-pyroglutamic acid is used in the synthesis of peptide-based drugs. Pyroglutamic acid and its derivatives play important roles in modulating the biological activity of peptides. By incorporating Boc-L-pyroglutamic acid into peptide sequences, researchers can develop compounds that target specific biological pathways, including those involved in neurological and immune functions. These peptides have potential applications in the treatment of diseases such as Alzheimer’s and other neurodegenerative disorders.

Boc-L-pyroglutamic acid is also utilized in the creation of peptidomimetics. The cyclic structure of pyroglutamic acid offers stability and rigidity to peptides, making it an attractive candidate for designing peptidomimetics that mimic natural peptides while providing enhanced resistance to enzymatic degradation. These peptidomimetics can be used for drug discovery and development, offering improved bioavailability and therapeutic potential.

Additionally, this compound plays an important role in the study of protein folding and structure. The incorporation of Boc-L-pyroglutamic acid into peptide sequences can help researchers understand how cyclic amino acids influence the stability and conformation of proteins. This knowledge is essential for designing more stable and effective therapeutic proteins and for exploring the structure-function relationship in protein engineering.

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.