L-Pyroglutamic acid
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L-Pyroglutamic acid

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L-Pyroglutamic acid is a cyclized derivative of L-glutamic acid.
Protein supplement in health care products.

Category
Cyclic Amino Acids
Catalog number
BAT-008077
CAS number
98-79-3
Molecular Formula
C5H7NO3
Molecular Weight
129.11
L-Pyroglutamic acid
IUPAC Name
(2S)-5-oxopyrrolidine-2-carboxylic acid
Synonyms
Pyroglutamic acid; Pidolic acid; H-Pyr-OH; 5-oxo-L-proline; (2S)-5-oxopyrrolidine-2-carboxylic acid
Appearance
White crystalline powder
Purity
95%
Density
1.38 g/cm3
Melting Point
158-162 °C
Boiling Point
453.1°C at 760 mmHg
Storage
Store at RT
Solubility
Soluble in Dichloromethane, DMSO, Methanol, Water
InChI
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
InChI Key
ODHCTXKNWHHXJC-VKHMYHEASA-N
Canonical SMILES
C1CC(=O)NC1C(=O)O

L-Pyroglutamic acid, also known as 5-oxoproline, is a cyclic derivative of the amino acid glutamic acid. It is formed when the γ-carboxyl group of glutamic acid reacts with its α-amino group, creating a lactam ring structure. This compound plays a crucial role in various biochemical processes, including protein synthesis and cellular metabolism. L-Pyroglutamic acid is often found in natural peptides and is considered an important intermediate in the biosynthesis of other amino acids.

One of the primary applications of L-Pyroglutamic acid is in peptide synthesis. It is commonly used as a building block in the production of cyclic peptides due to its unique structural features. The lactam ring structure of L-Pyroglutamic acid provides stability and rigidity to the peptide, making it an ideal component for designing peptides with enhanced biological activity. These peptides can be used in drug development, especially for diseases where stability is crucial for therapeutic efficacy.

L-Pyroglutamic acid is also employed in the development of bioactive compounds and pharmaceuticals. Its involvement in various metabolic pathways, particularly in the synthesis of glutathione, makes it an important compound for applications related to oxidative stress and cellular protection. Researchers have explored its potential in the treatment of neurodegenerative diseases and oxidative stress-related conditions, where enhancing glutathione levels can offer therapeutic benefits. The stability and biological relevance of L-Pyroglutamic acid make it an attractive target in drug design.

Another key application of L-Pyroglutamic acid is in the field of cosmetics and personal care products. It is used in formulations aimed at improving skin health and reducing the appearance of fine lines and wrinkles. L-Pyroglutamic acid’s ability to act as an antioxidant helps protect the skin from damage caused by free radicals. Additionally, its role in cellular metabolism makes it beneficial in promoting skin regeneration and maintaining skin hydration, making it a common ingredient in anti-aging creams and lotions.

Finally, L-Pyroglutamic acid is also utilized in the food and beverage industry as a flavor enhancer. Its umami taste and ability to modify flavor profiles make it a valuable ingredient in processed foods, especially in savory products. The compound can help boost the overall taste experience by enhancing natural flavors and reducing the need for artificial additives. Its use as a flavor enhancer is popular in the production of soups, sauces, and seasonings, where its natural origins are a desirable attribute.

1. Influence of l-pyroglutamic acid on the color formation process of non-enzymatic browning reactions.
Lothar W Kroh, Martin Kaufmann, Steffen Wegener. Food Chem. 2017 Oct 1; 232: 450-454. DOI: 10.1016/j.foodchem.2017.04.046. PMID: 28490097.
Heating aqueous d-glucose model reactions with l-glutamine and l-alanine yielded similar colored solutions. However, size-exclusion chromatography (SEC) revealed that both non-enzymatic browning reactions proceeded differently. Due to a fast occurring cyclization of l-glutamine to pyroglutamic acid, the typical amino-carbonyl reaction was slowed down. However, l-glutamine and l-alanine model reactions showed the same browning index. Closer investigations could prove that l-pyroglutamic acid was able to influence non-enzymatic browning reactions. SEC analyses of d-glucose model reactions with and without l-pyroglutamic acid revealed an increase of low molecular colored compounds in the presence of l-pyroglutamic acid. Polarimetric measurements showed a doubling of d-glucose mutarotation velocity and HPLC analyses of d-fructose formation during thermal treatment indicated a tripling of aldose-ketose transformation in the presence of l-pyroglutamic acid, which are signs of a faster proceeding non-enzymatic browning process. 2-Pyrrolidone showed no such behavior, thus the additional carboxylic group should be responsible for the observed effects.
2. Synthesis and bioactivities evaluation of l-pyroglutamic acid analogues from natural product lead.
Xiao-Ting Li, Wen-Jun Wu, Fang-Li Gang, Feng Zhu, Jie-Lu Wei, Ji-Wen Zhang. Bioorg Med Chem. 2018 Sep 1; 26(16): 4644-4649. DOI: 10.1016/j.bmc.2018.07.041. PMID: 30119995.
A series of l-pyroglutamic acid analogues from natural product lead were designed and synthesized, as well as their antifungal activities against Phytophthora infestans, neuritogenic activities, antibacterial activities and anti-inflammatory activities are described. The bioassays and SAR study showed that the majority of l-pyroglutamic acid esters have a significant antifungal activity against P. infestans, especially 2d and 2j demonstrated the best activities with EC50values of 1.44 and 1.21 μg mL-1, which were about seven times that of commercial azoxystrobin (7.85 μg mL-1). Moreover, compounds 2e, 2g and 4d displayed anti-inflammatory activity against LPS-induced NO production in BV-2 microglial cells; neuritogenic activity in NGF-induced PC-12 cells is the same activity. This study demonstrates that compounds 2d and 2j are potential drugs to control P. infestans.
3. A new endogenous anxiolytic agent: l-pyroglutamic acid.
M Beni, F Moroni, D E Pellegrini-Giampietro. Fundam Clin Pharmacol. 1988; 2(2): 77-82. DOI: 10.1111/j.1472-8206.1988.tb00623.x. PMID: 2455680.
By use of a simple anticonflict procedure (Vogel test), it was demonstrated that L-pyroglutamic acid (L-pyrrolidone carboxylic acid [L-PCA]), an amino acid naturally occurring in mammalian tissues and fluids, possesses anxiolytic activity. This tissues and fluids, possesses anxiolytic activity. This effect was stereospecific (D-PCA was inactive) and, in the rat, it was not associated with a decrease in motor activity. Ro 15-1788, a benzodiazepine antagonist, did not modify L-PCA actions. Furthermore, anxiolytic doses of the amino acid did not change the content of 5-hydroxytryptamine (5-HT) or of 5-hydroxyindoleacetic acid (5-HIAA) in the rat cortex and hippocampus. These results suggest that the mechanism of the anxiolytic activity of L-PCA is different from that of the benzodiazepines and of 5-HT1a agonists.
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