L-Glutamic acid α-4-methoxy-β-naphthylamide
Need Assistance?
  • US & Canada:
    +
  • UK: +

L-Glutamic acid α-4-methoxy-β-naphthylamide

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

A substrate for aminopeptidase A.

Category
γ−Amino acids
Catalog number
BAT-004244
CAS number
74938-90-2
Molecular Formula
C16H18N2O4
Molecular Weight
302.30
L-Glutamic acid α-4-methoxy-β-naphthylamide
IUPAC Name
(4S)-4-amino-5-[(4-methoxynaphthalen-2-yl)amino]-5-oxopentanoic acid
Synonyms
L-Glu-4MβNA; H-GLU-4M-BETANA; GLUTAMIC ACID-4M-BETANA
Appearance
Yellowish powder
Purity
≥ 98% (TLC)
Melting Point
183-186 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H18N2O4/c1-22-14-9-11(8-10-4-2-3-5-12(10)14)18-16(21)13(17)6-7-15(19)20/h2-5,8-9,13H,6-7,17H2,1H3,(H,18,21)(H,19,20)/t13-/m0/s1
InChI Key
JKMBFBPDQHOZTG-ZDUSSCGKSA-N
Canonical SMILES
COC1=CC(=CC2=CC=CC=C21)NC(=O)C(CCC(=O)O)N
1. II. Glutamine and glutamate
H Tapiero, G Mathé, P Couvreur, K D Tew 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.
2. L-Theanine reduces psychological and physiological stress responses
Kenta Kimura, Makoto Ozeki, Lekh Raj Juneja, Hideki Ohira Biol Psychol. 2007 Jan;74(1):39-45. doi: 10.1016/j.biopsycho.2006.06.006. Epub 2006 Aug 22.
L-Theanine is an amino acid contained in green tea leaves which is known to block the binding of L-glutamic acid to glutamate receptors in the brain. Because the characteristics of L-Theanine suggest that it may influence psychological and physiological states under stress, the present study examined these possible effects in a laboratory setting using a mental arithmetic task as an acute stressor. Twelve participants underwent four separate trials: one in which they took L-Theanine at the start of an experimental procedure, one in which they took L-Theanine midway, and two control trials in which they either took a placebo or nothing. The experimental sessions were performed by double-blind, and the order of them was counterbalanced. The results showed that L-Theanine intake resulted in a reduction in the heart rate (HR) and salivary immunoglobulin A (s-IgA) responses to an acute stress task relative to the placebo control condition. Moreover, analyses of heart rate variability indicated that the reductions in HR and s-IgA were likely attributable to an attenuation of sympathetic nervous activation. Thus, it was suggested that the oral intake of L-Theanine could cause anti-stress effects via the inhibition of cortical neuron excitation.
3. GABA and glutamate in the human brain
Ognen A C Petroff 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.
Online Inquiry
Verification code
Inquiry Basket