L-Pyroglutamic acid ethyl ester
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L-Pyroglutamic acid ethyl ester

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Cyclic Amino Acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
L-Pyroglutamic acid ethyl ester
ethyl (2S)-5-oxopyrrolidine-2-carboxylate
White to yellowish crystalline powder
≥ 98% (HPLC)
1.161 g/cm3
Melting Point
50-58 °C
Store at 2-8°C
InChI Key
Canonical SMILES
1. N-acetylcysteine ethyl ester as GSH enhancer in human primary endothelial cells: A comparative study with other drugs
Daniela Giustarini, Federico Galvagni, Isabella Dalle Donne, Aldo Milzani, Filiberto Maria Severi, Annalisa Santucci, Ranieri Rossi Free Radic Biol Med. 2018 Oct;126:202-209. doi: 10.1016/j.freeradbiomed.2018.08.013. Epub 2018 Aug 14.
Several drugs are currently in use as glutathione (GSH) enhancers in clinical, pre-clinical and experimental research. Here we compare the ability of N-acetylcysteine (NAC), 2-oxothiazolidine-4-carboxylic acid (OTC), glutathione ethyl ester (GSH-EE) and N-acetylcysteine ethyl ester (NACET) to increase the intracellular concentration of GSH using primary human umbilical vein endothelial cells (HUVEC) as in vitro model. Our experiments highlighted that NACET is largely the most efficient molecule in increasing the intracellular levels of GSH, cysteine, and γ-glutamylcysteine. This is because NACET is lipophilic and can freely cross plasma membrane but, inside the cell, it is de-esterified to the more hydrophilic NAC, which, in turn, is trapped into the cell and slowly transformed into cysteine. The higher availability of cysteine is matched by an increase in GSH synthesis, cysteine availability being the rate limiting step for this reaction. Surprisingly, the increase in GSH concentration was not linear but peaked at 0.5 mM NACET and gradually decreased when cells were treated with higher concentrations of NACET. We demonstrated that this puzzling ceiling effect was due to the fact that NAC released from NACET turned out to be a competitive inhibitor of the enzyme glutamate-cysteine ligase, with a Ki value of 3.2 mM. By using a cell culture medium lacking of cysteine and methionine, we could demonstrate that the slight increase in intracellular levels of cysteine and GSH induced by NAC in HUVEC grown in standard medium was due to the reduction of the cystine present in the medium itself there rather than to the action of NAC as Cys pro-drug. This fact may explain why NAC works well as GSH enhancer at very high concentrations in pre-clinical and in vitro studies, whereas it failed in most clinical trials.
2. Montelukast-loaded nanostructured lipid carriers: part I oral bioavailability improvement
Arpana Patil-Gadhe, Varsha Pokharkar Eur J Pharm Biopharm. 2014 Sep;88(1):160-8. doi: 10.1016/j.ejpb.2014.05.019. Epub 2014 May 27.
The purpose of the study was to formulate montelukast-loaded nanostructured lipid carrier (MNLC) to improve its systemic bioavailability, avoid hepatic metabolism and reduce hepatic cellular toxicity due to metabolites. MNLC was prepared using melt-emulsification-homogenization method. Preformulation study was carried out to evaluate drug-excipient compatibility. MNLCs were prepared using spatially different solid and liquid lipid triglycerides. CAE (DL-Pyrrolidonecarboxylic acid salt of L-cocyl arginine ethyl ester), a cationic, biodegradable, biocompatible surfactant was used to stabilize the system. MNLCs were characterized by FTIR, XRPD and DSC to evaluate physicochemical properties. MNLCs having a particle size of 181.4 ± 6.5 nm with encapsulation efficiency of 96.13 ± 0.98% were prepared. FTIR findings demonstrated no interaction between the drug and excipients of the formulation which could lead to asymmetric vibrations. DSC and XRPD study confirmed stable amorphous form of the montelukast in lipid matrix. In vitro release study revealed sustained release over a period of 24 h. In vivo single dose oral pharmacokinetic study demonstrated 143-fold improvement in bioavailability as compared to montelukast-aqueous solution. Thus, the result of this study implies that developed MNLC formulation be suitable to sustain the drug release with improvement in the bioavailability.
3. Quantitation and sensory properties of three newly identified pyroglutamyl oligopeptides in sake
Katsumi Hashizume, Toshihiko Ito, Yusuke Nagae, Tetsuo Tokiwano Biosci Biotechnol Biochem. 2019 Feb;83(2):357-364. doi: 10.1080/09168451.2018.1530095. Epub 2018 Oct 8.
Three new peptides: (pGlu)L-ethyl, (pGlu)LFGP-ethyl and (pGlu)LFNP-ethyl, were identified in the search for pyroglutamyl oligopeptide ethyl esters in sake. The ethyl esterified peptides in sake were quantitated using stable isotope dilution analysis and additional quantitation of (pGlu)L was performed using an external standard method. The concentrations of (pGlu)L-ethyl and (pGlu)L in 33 commercial sake samples ranged from 0.16 to 1.57 mg/L and 1.49 to 7.55 mg/L, respectively. The sensory properties of the pyroglutamyl oligopeptide ethyl esters and corresponding non-esterified peptides were examined: the estimated difference threshold of (pGlu)L (2.0 mg/L) and (pGlu)L-ethyl (0.267 mg/L) was exceeded in 32 and 26 samples, respectively. Estimated thresholds of (pGlu)LFGP-ethyl and (pGlu)LFNP-ethyl were often lower than the levels in quantitated sake samples. The sensory effects of these pyroglutamyl dipeptides on a model sake quality may be negative because of their unpleasant taste, however, (pGlu)LFNP-ethyl may be positive because of its mild taste.
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