L-Glutamic acid
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L-Glutamic acid

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L-glutamic acid is a non-essential amino acid that acts as an excitatory neurotransmitter in the CNS.

Category
L-Amino Acids
Catalog number
BAT-014298
CAS number
56-86-0
Molecular Formula
C5H9NO4
Molecular Weight
147.13
L-Glutamic acid
IUPAC Name
(2S)-2-aminopentanedioic acid
Synonyms
Glutamic acid, L-; (+)-L-Glutamic acid; (2S)-2-Azaniumyl-5-hydroxy-5-oxopentanoate; (S)-(+)-Glutamic acid; (S)-2-Amino-1,5-pentanedioic acid; (S)-2-Aminopentanedioic acid; (S)-Glutamic acid; 2-Aminoglutaric acid; L-(+)-Glutamic acid; L-Glutaminic acid; L-α-Aminoglutaric acid; Aciglut; E 620; Glusate; Glutacid; Glutamic acid; Glutamicol; Glutamidex; Glutaminic acid; Glutaminol; Glutaton; l-Glutaminic acid; NSC 143503; Pentanedioic acid, 2-amino-, (S)-; Sortem; α-Aminoglutaric acid; α-Glutamic acid
Related CAS
138-16-9 (Deleted CAS) 6899-05-4 (Deleted CAS) 10549-13-0 (Deleted CAS) 2087491-17-4 (Deleted CAS)
Appearance
White to Almost White Crystalline Powder
Purity
>98%
Density
1.46 g/cm3
Melting Point
224°C (dec.)
Boiling Point
333.8±32.0°C at 760 mmHg
Storage
Store at RT
Solubility
Soluble in 1 M HCl: 100 mg/mL.
InChI
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
InChI Key
WHUUTDBJXJRKMK-VKHMYHEASA-N
Canonical SMILES
C(CC(=O)O)C(C(=O)O)N
1.Recent Advances in Poly(α- L-glutamic acid)-Based Nanomaterials for Drug Delivery
Biomolecules. 2022 Apr 25;12(5):636. doi: 10.3390/biom12050636.
Poly( α - L -glutamic acid) (PGA) is a class of synthetic polypeptides composed of the monomeric unit α - L -glutamic acid. Owing to their biocompatibility, biodegradability, and non-immunogenicity, PGA-based nanomaterials have been elaborately designed for drug delivery systems. Relevant studies including the latest research results on PGA-based nanomaterials for drug delivery have been discussed in this work. The following related topics are summarized as: (1) a brief description of the synthetic strategies of PGAs; (2) an elaborated presentation of the evolving applications of PGA in the areas of drug delivery, including the rational design, precise fabrication, and biological evaluation; (3) a profound discussion on the further development of PGA-based nanomaterials in drug delivery. In summary, the unique structures and superior properties enables PGA-based nanomaterials to represent as an enormous potential in biomaterials-related drug delivery areas.
2.GABA and glutamate in the human brain
Neuroscientist. 2002 Dec;8(6):562-73. doi: 10.1177/1073858402238515.
Cortical excitability reflects a balance between excitation and inhibition. Glutamate is the main excitatory and GABA the main inhibitory neurotransmitter in the mammalian cortex. Changes in glutamate and GABA metabolism may play important roles in the control of cortical excitability. Glutamate is the metabolic precursor of GABA, which can be recycled through the tricarboxylic acid cycle to synthesize glutamate. GABA synthesis is unique among neurotransmitters, having two separate isoforms of the rate-controlling enzyme, glutamic acid decarboxylase. The need for two separate genes on two chromosomes to control GABA synthesis is unexplained. Two metabolites of GABA are present in uniquely high concentrations in the human brain. Homocarnosine and pyrrolidinone have a major impact on GABA metabolism in the human brain. Both of these GABA metabolites have anticonvulsant properties and can have a major impact on cortical excitability.
3.II. Glutamine and glutamate
Biomed Pharmacother. 2002 Nov;56(9):446-57. doi: 10.1016/s0753-3322(02)00285-8.
Glutamine and glutamate with proline, histidine, arginine and ornithine, comprise 25% of the dietary amino acid intake and constitute the "glutamate family" of amino acids, which are disposed of through conversion to glutamate. Although glutamine has been classified as a nonessential amino acid, in major trauma, major surgery, sepsis, bone marrow transplantation, intense chemotherapy and radiotherapy, when its consumption exceeds its synthesis, it becomes a conditionally essential amino acid. In mammals the physiological levels of glutamine is 650 micromol/l and it is one of the most important substrate for ammoniagenesis in the gut and in the kidney due to its important role in the regulation of acid-base homeostasis. In cells, glutamine is a key link between carbon metabolism of carbohydrates and proteins and plays an important role in the growth of fibroblasts, lymphocytes and enterocytes. It improves nitrogen balance and preserves the concentration of glutamine in skeletal muscle. Deamidation of glutamine via glutaminase produces glutamate a precursor of gamma-amino butyric acid, a neurotransmission inhibitor. L-Glutamic acid is a ubiquitous amino acid present in many foods either in free form or in peptides and proteins. Animal protein may contain from 11 to 22% and plants protein as much as 40% glutamate by weight. The sodium salt of glutamic acid is added to several foods to enhance flavor. L-Glutamate is the most abundant free amino acid in brain and it is the major excitatory neurotransmitter of the vertebrate central nervous system. Most free L-glutamic acid in brain is derived from local synthesis from L-glutamine and Kreb's cycle intermediates. It clearly plays an important role in neuronal differentiation, migration and survival in the developing brain via facilitated Ca++ transport. Glutamate also plays a critical role in synaptic maintenance and plasticity. It contributes to learning and memory through use-dependent changes in synaptic efficacy and plays a role in the formation and function of the cytoskeleton. Glutamine via glutamate is converted to alpha-ketoglutarate, an integral component of the citric acid cycle. It is a component of the antioxidant glutathione and of the polyglutamated folic acid. The cyclization of glutamate produces proline, an amino acid important for synthesis of collagen and connective tissue. Our aim here is to review on some amino acids with high functional priority such as glutamine and to define their effective activity in human health and pathologies.
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