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3081-62-7

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3081-62-7 Usage

General Description

Gamma-Glutamylmethylamide is a chemical compound known for its role in the metabolism of glutathione, a critical antioxidant in plants, animals, fungi, and some bacteria and archaea. It is studied in the context of detoxifying harmful compounds in the body. This chemical is synthesized through the gamma-glutamyl cycle and involves the enzymatic action of gamma-glutamyltransferase. Possible links have been explored between abnormalities in gamma-Glutamylmethylamide levels and various health conditions, however further research is needed. gamma-glutamylmethylamide is typically found in biological samples such as blood and urine, and can be used as a biomarker.

Check Digit Verification of cas no

The CAS Registry Mumber 3081-62-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,8 and 1 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3081-62:
(6*3)+(5*0)+(4*8)+(3*1)+(2*6)+(1*2)=67
67 % 10 = 7
So 3081-62-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H12N2O3/c1-8-4(6(10)11)2-3-5(7)9/h4,8H,2-3H2,1H3,(H2,7,9)(H,10,11)/t4-/m0/s1

3081-62-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Methyl-L-glutamine

1.2 Other means of identification

Product number -
Other names N-Methylglutamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3081-62-7 SDS

3081-62-7Synthetic route

Copper(II); (S)-5-oxo-pyrrolidine-2-carboxylate

Copper(II); (S)-5-oxo-pyrrolidine-2-carboxylate

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
In methanol at 70℃; for 168h;26%
N2-benzyloxycarbonyl-N5-methyl-L-glutamine
95082-75-0

N2-benzyloxycarbonyl-N5-methyl-L-glutamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With palladium Hydrogenation;
L-glutamic acid-5-ethyl ester; hydrochloride
73270-47-0

L-glutamic acid-5-ethyl ester; hydrochloride

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With ethanol
methylamine
74-89-5

methylamine

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

L-glutamic acid 5-methyl ester
1499-55-4

L-glutamic acid 5-methyl ester

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
(i) CS2, MeOH, (ii) AcOH; Multistep reaction;
methylamine hydrochloride
593-51-1

methylamine hydrochloride

monosodium glutamate
142-47-2

monosodium glutamate

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
In water at 30℃; for 0.166667h; γ-glutamylmethylamide synthetase from Methylophaga sp. AA-30, 0.5 M Tris HCl buffer pH 7.5, 2.5 M 2-mercaptoethanol, 0.1 M MnCl2, 0.1 M ATP;
In water at 30℃; for 0.166667h; γ-glutamylmethylamide synthetase from Methylophaga sp. AA-30, 0.5 M Tris HCl buffer pH 7.5, 2.5 M 2-mercaptoethanol, 0.1 M MnCl2, 0.1 M ATP; relative enzyme activity, Km, effect of pH, temperature, metal ions;
L-glutamine
56-85-9

L-glutamine

methylamine
74-89-5

methylamine

A

L-glutamic acid
56-86-0

L-glutamic acid

B

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With glutaminase from Pseudomonas nitroreducens IFO 12694; imidazole buffer In water at 30℃; for 1h; Product distribution; other reagent, pH dependence;
L-glutamine
56-85-9

L-glutamine

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With glutaminase from Pseudomonas nitroreducens IFO 12694; imidazole buffer In water at 30℃; relative rate of glutamyl transfer;
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.333333h; pH=10.5; aq. buffer; Enzymatic reaction;
GLUTATHIONE
70-18-8

GLUTATHIONE

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With glutaminase from Pseudomonas nitroreducens IFO 12694; imidazole buffer In water at 30℃; relative rate of glutamyl transfer;
methylamine
74-89-5

methylamine

(S)-5-oxo-pyrrolidine-carboxylic acid-(2)

(S)-5-oxo-pyrrolidine-carboxylic acid-(2)

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With water at 37℃;
monosodium L-glutamate
142-47-2

monosodium L-glutamate

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With imidazole buffer; Pseudomonas taetrolens Y-30 glutamine synthetase EC 6.3.1.2; magnesium chloride; ATP at 30℃; pH=8.5; Enzyme kinetics; Further Variations:; pH-values; Reagents;
methylamine hydrochloride
593-51-1

methylamine hydrochloride

monosodium L-glutamate
142-47-2

monosodium L-glutamate

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With 1H-imidazole; ATP; magnesium chloride; Methylovorus mays No. 9 theanine-forming enzyme In water at 30℃; pH=7.75; Enzyme kinetics;
monosodium glutamate
142-47-2

monosodium glutamate

methylamine
74-89-5

methylamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
With recombinant (His)6-tagged Escherichia coli K12 W3110 γ-glutamylcysteine synthetase; magnesium sulfate; ATP In water at 37℃; for 1h; pH=8.5; aq. buffer; Enzymatic reaction;
γ-L-glutamyl-L-glutamine
10148-81-9

γ-L-glutamyl-L-glutamine

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase / 0.03 h / 30 °C / pH 10.5 / aq. buffer; Enzymatic reaction
2: recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase / 0.33 h / 30 °C / pH 10.5 / aq. buffer; Enzymatic reaction
View Scheme
tasiamide F

tasiamide F

A

N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

B

(R)-(-)-α-methylamino phenylacetic acid
30925-14-5

(R)-(-)-α-methylamino phenylacetic acid

C

L-proline
147-85-3

L-proline

Conditions
ConditionsYield
With hydrogenchloride In water at 110℃; for 24h;
N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

zinc(II) chloride
7646-85-7

zinc(II) chloride

[(L-γ-glutamyl-methylamide(-1H))2Zn]*0.8H2O

[(L-γ-glutamyl-methylamide(-1H))2Zn]*0.8H2O

Conditions
ConditionsYield
With lithium hydroxide In methanol ligand was reacted with LiOH; soln. of ZnCl2 in methanol was added at room temp.; washed (methanol); elem. anal.;63%
N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

2-oxo-glutaric acid-5-methylamide
26366-65-4

2-oxo-glutaric acid-5-methylamide

Conditions
ConditionsYield
With enzyme from the toxin of crotalus adamanteus; catalase
N-(γ-glutamyl)methylamine
3081-62-7

N-(γ-glutamyl)methylamine

A

L-glutamic acid
56-86-0

L-glutamic acid

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.0333333h; pH=10.5; aq. buffer; Enzymatic reaction;

3081-62-7Relevant articles and documents

Antidiabetic activity of Zn(II) complexes with a derivative of L-glutamine

Matsumoto, Kinuyo,Yamamoto, Shuhei,Yoshikawa, Yutaka,Doe, Matsumi,Kojima, Yoshitane,Sakurai, Hiromu,Hashimoto, Hiroko,Kajiwara, Naemi M.

, p. 1077 - 1081 (2005)

The insulinomimetic activity of zinc(II) complexes Zn(gln-m)2 and Zn(gln-e)2, respectively, with L-γ-glutamyl-methylamide (gln-m) and -ethylamide (theanine: gln-e), components of green tea, were compared to that of Zn(gln)2 with L-glutamine (gin) in an in vitro study using isolated rodent adipocytes treated with epinephrine in the presence of glucose, expressed as the IC50 value (50% inhibition concentration) of free fatty acids (FFA) released from fat cells. The former were found to have higher inslinomimetic activity than that of the latter. The IC50 values of the former were 0.61 and 0.56, respectively. Then, the anti-diabetic activity of a zinc(II) complex, Zn(gln-e)2, was examined in an in vivo experiment on KK-Aγ mice, model animals of type-2 DM, by the intraperitoneal (ip) injection of 3-4 mg Zn/kg b.w./day for 13 days. The blood-glucose level of a group treated with a Zn complex, Zn(gln-e)2, decreased significantly after 13 days compared to those of non-treated and gln-e treated groups. The serum concentrations of triglyceride (TG) and HbA1C decreased significantly in Zn(gln-e) 2 treated KK-Aγ mice compared to those of the gln-e treated group, respectively. Furthermore, the improvement in glucose tolerance was confirmed by an oral glucose tolerance test.

Peptide Tyrosinase Activators

-

, (2015/06/10)

Peptides that increase melanin synthesis are provided. These peptides include pentapeptides YSSWY, YRSRK, and their variants. The peptides may activate the enzymatic activity of tyrosinase to increase melanin synthesis. The pharmaceutical, cosmetic, and other compositions including the peptides are also provided. The methods of increasing melanin production in epidermis of a subject are provided where the methods include administering compositions comprising an amount of one or more peptides effective to increase the melanin production. The methods also include treating vitiligo or other hypopigmentation disorders with compositions including one or more peptides.

A novel catalytic ability of γ-glutamylcysteine synthetase of Escherichia coli and its application in theanine production

Miyake, Koichiro,Kakita, Shingo

experimental part, p. 2677 - 2683 (2010/09/11)

γ-Glutamylcysteine synthetase (γGCS, EC 6.3.2.2) catalyzes the formation of γ-glutamylcysteine from L-glutamic acid (Glu) and L-cysteine (Cys) in an ATP-dependent manner. While γGCS can use various amino acids as substrate, little is known about whether it can use non-amino acid compounds in place of Cys. We determined that γGCS from Escherichia coli has the ability to combine Glu and amines to form γ-glutamylamides. The reaction rate depended on the length of the methylene chain of the amines in the following order: n-propylamine > butylamine > ethylamine methylamine. The optimal pH for the reaction was narrower and more alkaline than for the reaction with an amino acid. The newly found catalytic ability of γGCS was used in the production of theanine (γ-glutamylethylamine). The resting cells of E. coli expressing γGCS, in which ATP was regenerated through glycolysis, synthesized 12.1 mm theanine (18 h) from 429 mm ethylamine.

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