56488-60-9

Basic information

• Product Name: Glutaurine
• Synonyms: Glutaurine;glutaurin;Litoralon;L-γ-Glutamyltaurine;Nδ-(2-Sulfoethyl)-L-glutamine;γ-Glutamyltaurine;γ-Glu-Tau;gamma-L-Glutamyltaurine
• CAS NO: 56488-60-9
• Molecular Formula: C₇H₁₄N₂O₆S
• Molecular Weight: 254.262
• Mol File: 56488-60-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 223-226 °C
• Appearance: /
• Density: 1.52g/cm³
• Refractive Index: 1.556
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.40±0.50(Predicted)
• CAS DataBase Reference: Glutaurine(CAS DataBase Reference)
• NIST Chemistry Reference: Glutaurine(56488-60-9)
• EPA Substance Registry System: Glutaurine(56488-60-9)

Safety Data

• Hazardous Substances Data: 56488-60-9(Hazardous Substances Data)

Usage

Description

Glutaurine, also known as γ-aminobutyric acid (GABA), is a non-protein amino acid that functions as an inhibitory neurotransmitter in the vertebrate central nervous system. It plays a crucial role in reducing neuronal excitability and is involved in various physiological processes, including the regulation of muscle tone, immune function, and the maintenance of cellular osmotic balance.

Uses

Used in Pharmaceutical Applications:
Glutaurine is used as an antiepileptic agent for its ability to reduce seizure activity and improve overall brain function. It helps in stabilizing the electrical activity of the brain, thus providing relief from epileptic seizures.
Used in Cognitive Enhancement:
Glutaurine is used as a cognitive enhancer for its anti-amnesia properties, which help improve memory and learning capabilities. It supports the overall cognitive function by promoting the synthesis of proteins and neurotransmitters essential for brain health.
Used in Anxiety Management:
Glutaurine is used as an anxiolytic agent, mimicking the effects of the anxiolytic drug Diazepam (D416855). It helps in reducing anxiety levels by promoting relaxation and a sense of calm, making it a potential candidate for the treatment of anxiety disorders.
Used in Sports Nutrition:
Glutaurine is used as a sports supplement for its role in muscle recovery and growth. It aids in the reduction of muscle cramps and soreness, enhancing athletic performance and overall physical endurance.
Used in Detoxification:
Glutaurine is used as a detoxifying agent, helping the body eliminate harmful substances and toxins. It supports the liver's detoxification processes and promotes overall health and well-being.
Used in Immune System Support:
Glutaurine is used as an immune system booster, playing a vital role in the regulation of immune cell function and the maintenance of a healthy immune response.
Used in Osmotic Balance:
Glutaurine is used to maintain cellular osmotic balance, preventing cell damage and supporting overall cellular health. It helps in the regulation of fluid balance within cells, ensuring their proper functioning and integrity.

InChI:InChI=1/C7H14N2O6S/c8-5(7(11)12)1-2-6(10)9-3-4-16(13,14)15/h5H,1-4,8H2,(H,9,10)(H,11,12)(H,13,14,15)/t5-/m0/s1

Synthetic route

α-benzyl-γ-L-glutamyltaurine (58238-09-8) → Glutaurine (56488-60-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water; acetic acid for 20h; Ambient temperature;	92%
With formic acid; hydrogen; dihydrogen peroxide; palladium on activated charcoal for 10h; Yield given;

L-glutamine (56-85-9) + Tau (107-35-7) → Glutaurine (56488-60-9)

Conditions	Yield
With γ-glutamyltranspeptidase In water at 25℃; for 48h;	36%

Tau (107-35-7) + monosodium L-glutamate (142-47-2) → Glutaurine (56488-60-9)

Conditions	Yield
With adenosine 5'-triphosphate sodium salt; magnesium chloride; bovine serum albumin at 30℃; for 24h; γ-glutamylcysteine synthetase from Proteus mirabilis, pH 8.5;	24.5%

L-Glutaminsaeure-γ-(2-chloraethyl)-amid (4821-79-8) → Glutaurine (56488-60-9)

Conditions	Yield
With sodium sulfite In water for 48h; Ambient temperature; Yield given;

Sodium; 2-((S)-4-benzyloxycarbonyl-4-benzyloxycarbonylamino-butyrylamino)-ethanesulfonate → Glutaurine (56488-60-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water; acetic acid Yield given;

Cbz-(L)-Glu-OBn (3705-42-8) → Glutaurine (56488-60-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: EDC 2: hydrogen / Pd-C 3: sodium sulfite / H2O / 48 h / Ambient temperature View Scheme

L-N-Carbobenzoxy-glutaminsaeure-α-benzylester-γ-(2-chloraethyl)-amid (4821-78-7) → Glutaurine (56488-60-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / Pd-C 2: sodium sulfite / H2O / 48 h / Ambient temperature View Scheme

Boc-Glu-OBn (30924-93-7) → Glutaurine (56488-60-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / EDC / CH2Cl2 / 20 h / Ambient temperature 2: HCOOH, 30percent H2O2 / 20 h / Ambient temperature 3: H2, 98percent aq. HCOOH, 30percent H2O2 / 10percent Pd/C / 10 h View Scheme
Multi-step reaction with 2 steps 1: 1) N-hydroxy-5-norbornene-2,3-dicarboximide/DCC, 2) NaHCO3, 3) Amberlite IR-120B (H+ form) 2: 92 percent / H2 / Pd-C / acetic acid; methanol; H2O / 20 h / Ambient temperature View Scheme

Boc-L-Glu(NHCH2CH2SAc)-OBzl → Glutaurine (56488-60-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCOOH, 30percent H2O2 / 20 h / Ambient temperature 2: H2, 98percent aq. HCOOH, 30percent H2O2 / 10percent Pd/C / 10 h View Scheme

Boc-Glu(OBzl)-OH (13574-13-5) + Glutaurine (56488-60-9) → γ-benzyl-α-L-glutamyltaurine (141870-97-5)

Conditions	Yield
With N-hydroxy-5-norbornene-2,3-dicarboximide; Amberlite IR-120B (H+ form); sodium hydrogencarbonate; dicyclohexyl-carbodiimide Yield given. Multistep reaction;

Glutaurine (56488-60-9) → Sodium; 2-((S)-4-amino-4-carboxy-butyrylamino)-ethanesulfonate (122546-59-2)

Conditions	Yield
With sodium hydrogencarbonate In water

ethanol (64-17-5) + Glutaurine (56488-60-9) → glutaurine ethyl ester

Conditions	Yield
With sulfuric acid for 1h; Heating;

Glutaurine (56488-60-9) + acetyl chloride (75-36-5) → N1,N2-diacetylglutaurine

Conditions	Yield
With pyridine for 2h; Reflux;

Glutaurine (56488-60-9) + methyl iodide (74-88-4) → N1-methyl-N2-dimethylglutaurine

Conditions	Yield
for 6h; Reflux;

Upstream product

• 107-35-7 Tau 
• 142-47-2 monosodium L-glutamate 
• 30924-93-7 Boc-Glu-OBn 
• 4821-78-7 L-N-Carbobenzoxy-glutaminsaeure-α-benzylester-γ-(2-chloraethyl)-amid 
• 3705-42-8 Cbz-(L)-Glu-OBn 
• 58238-09-8 α-benzyl-γ-L-glutamyltaurine 
• 4821-79-8 L-Glutaminsaeure-γ-(2-chloraethyl)-amid 
• 56-85-9 L-glutamine 

Downstream Products

• 141870-97-5 γ-benzyl-α-L-glutamyltaurine 

Relevant articles and documents

CALCIUM RECEPTOR ACTIVATOR

A calcium receptor activator containing one or more kinds of substances selected from á-Glu-Cys-Gly, á-Glu-Cys(SNO)-Gly, á-Glu-Ala, á-Glu-Gly, á-Glu-Cys, á-Glu-Met, á-Glu-Thr, á-Glu-Val, á-Glu-Orn, Asp-Gly, Cys-Gly, Cys-Met, Glu-Cys, Gly-Cys, Leu-Asp, D-Cys, á-Glu-Met(O), á-Glu-Val-Val, á-Glu-Val-Glu, á-Glu-Val-Lys, á-Glu- á-Glu-Val, á-Glu-Val-NH2, á-Glu-Val-ol, á-Glu-Ser, á-Glu-Tau, á-Glu-Cys(S-Me)(O), á-Glu-Leu, á-Glu-Ile, á-Glu-t-Leu, á-Glu-Cys(S-allyl)-Gly, á-Glu-Gly-Gly, á-Glu-Val-Phe, á-Glu-Val-Ser, á-Glu-Val-Pro, á-Glu-Val-Arg, á-Glu-Val-Asp, á-Glu-Val-Met, á-Glu-Val-Thr, á-Glu-Val-His, á-Glu-Val-Asn,á-Glu-Val-Gln, á-Glu-Val-Cys, á-Glu-Val-Orn, á-Glu-Ser-Gly, á-Glu-Cys(S-Me), á-Glu-Abu-Gly, á-Glu-Cys(S-Me)-Gly, and á-Glu-Val-Gly.

α-Benzyl-γ-L-glutamyltaurine as a useful intermediate for the synthesis of a brain-peptide, γ-L-glutamyltaurine

The synthesis of a neuropeptide, γ-L-glutamyltaurine (3a), was achieved via α-benzyl-γ-L-glutamyltaurine (2a) as a useful intermediate, which was prepared from α-benzyl N-tert-butoxycarbonyl-r-glutamate (1a) and taurine (2-aminoethanesulfonic acid) by active ester method. The preparation of its α-isomer 3b was also described.

Simple peptides. III. Syntheses and properties of taurine-oligopeptides containing an acidic alpha-amino acid.

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