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

Uses

Glutaurine has been observed to display antiepileptic effects with anti-amnesia properties. Mimics anxiolytic drug Diazepam (D416855).

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

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

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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