1955-67-5

Basic information

• Product Name: AMINO ACID HYDROXAMATES L-GLUTAMIC ACID GAMMA-MONOHYDROXAMATE
• Synonyms: (4S)-4-Amino-4-carboxybutanehydroxamic acid;(S)-4-Amino-4-carboxybutanehydroximic acid;3-[2-Oxo-2-(hydroxyamino)ethyl]alanine;L-Glutamic acid γ-hydroxamate;N5-Hydroxy-L-glutamine;(2S)-5-amino-2-(hydroxyamino)-5-keto-valeric acid;(2S)-5-amino-2-(hydroxyamino)-5-oxopentanoic acid;(2S)-5-azanyl-2-(hydroxyamino)-5-oxo-pentanoic acid
• CAS NO: 1955-67-5
• Molecular Formula: C₅H₁₀N₂O₄
• Molecular Weight: 162.14
• Mol File: 1955-67-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 154 °C
• Boiling Point: 553.6°Cat760mmHg
• Flash Point: 288.6°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 1.46E-14mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: −20°C
• PKA: 2.21±0.10(Predicted)
• CAS DataBase Reference: AMINO ACID HYDROXAMATES L-GLUTAMIC ACID GAMMA-MONOHYDROXAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: AMINO ACID HYDROXAMATES L-GLUTAMIC ACID GAMMA-MONOHYDROXAMATE(1955-67-5)
• EPA Substance Registry System: AMINO ACID HYDROXAMATES L-GLUTAMIC ACID GAMMA-MONOHYDROXAMATE(1955-67-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1955-67-5(Hazardous Substances Data)

Usage

Uses

L-Glutamic acid γ-monohydroxamate has been used as a standard to calculate transglutaminase (TGase) activity.

Definition

ChEBI: A hydroxamic acid that is L-glutamine hydroxylated at N-5.

Biochem/physiol Actions

L-Glutamic acid γ-monohydroxamate [L-Glu(gamma)HXM] is used as a vanadium ligand which potentiates vanadiums metabolic activity. L-Glu(gamma)HXM is also used as a substrate for E. coli asparagine synthetase B and as an ATP-dependent irreversible inhibitor of Escherichia coli gamma-glutamylcysteine synthetase.

InChI:InChI=1/C5H10N2O4/c6-4(8)2-1-3(7-11)5(9)10/h3,7,11H,1-2H2,(H2,6,8)(H,9,10)/t3-/m0/s1

Upstream product

• 142-47-2 monosodium L-glutamate 
• 56-86-0 L-glutamic acid 
• 10148-81-9 L-γ-glutamyl-L-glutamine 
• 70-18-8 GLUTATHIONE 
• 56-85-9 L-glutamine 
• 3183-72-0 N-γ-L-glutamyl-4-aminobutyric acid 
• 1119-33-1 (S)-2-Amino-pentanedioic acid 5-ethyl ester 

Downstream Products

• 56-86-0 L-glutamic acid 
• 20292-78-8 amino phosphoric acid 
• 98-79-3 L-Pyroglutamic acid 

Relevant articles and documents

Molecular cloning and characterization of γ-Glutamyltranspeptidase from pseudomonas nitroreducens IFO12694

y-Glutamyltranspeptidase from Pseudomonas nitroreducens IFO12694 (PnGGT) exhibited higher hydro-lytic activity than transfer activity, as compared with other y-glutamyltranspeptidases (GGTs). PnGGT showed little activity towards most of L-amino acids and towards glycyl-glycine, which is often used as a standard y-glutamyl accepter in GGT transfer reactions. The preferred substrates for PnGGT as a y-glutamyl accepter were amines such as methylamine, ethylamine, and isopropylamine.

γ-Glutamyl Transfer Reactions by Glutaminase from Pseudomonas nitroreducens IFO 12694 and Their Application for the Syntheses of Theanine and γ-Glutamylmethylamide

In a mixture containing γ-glutamyl donor (donor) and γ-glutamyl acceptor (acceptor), the glutaminase of Pseudomonas nitroreducens IFO 12694 simultaneously catalyzed a γ-glutamyl transfer reaction and hydrolysis of the donor. The variation of the activities responding to the concentration of glutathione and glycylglycine indicated that the enzyme might be classified in a group of glutaminases that shows hydrolysis prior to transfer reaction. On the other hand, the results with glutamine and ethylamine or methylamine indicated that the enzyme was active in the transfer reaction with suppressed hydrolysis of glutamine, and suggested the possibility of using the reaction for producing γ-glutamylethylamide (theanine) or γ-glutamylmethylamide (γ-GMA). In fact, in a mixture containing high concentrations of substrates (0.7 M glutamine, 1.5 M ethylamine or methylamine) and 0.5 unit/ml glutaminase (borate buffer pH 11), 270 mM (47 g/L) theanine or 250 mM (38 g/L) γ-GMA was formed in 7 h of incubation at 30°C.