74817-54-2

Basic information

• Product Name: D-GLUTAMINE METHYL ESTER HYDROCHLORIDE
• Synonyms: D-GLUTAMINE METHYL ESTER HCL;D-GlutaMine Methyl ester hydrochloride/(R)-Methyl 2,5-diaMino-5-oxopentanoate hydrochloride;D-Glutamine, methyl ester, hydrochloride (1:1);D-GLUTAMINE METHYL ESTER HYDROCHLORIDE;H-D-GLN-OME HCL;(R)-2-AMINO-4-CARBAMOYL-BUTYRIC ACID METHYL ESTER, HCL;METHYL D-GLUTAMINATE;(R)-Methyl 2,5-diamino-5-oxopentanoate hydrochloride
• CAS NO: 74817-54-2
• Molecular Formula: C₆H₁₂N₂O₃*ClH
• Molecular Weight: 196.63
• Product Categories: chiral
• Mol File: 74817-54-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 344.6 °C at 760 mmHg
• Flash Point: 199 °C
• Appearance: /
• Density: 1.178g/cm3
• Vapor Pressure: 6.52E-05mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: D-GLUTAMINE METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: D-GLUTAMINE METHYL ESTER HYDROCHLORIDE(74817-54-2)
• EPA Substance Registry System: D-GLUTAMINE METHYL ESTER HYDROCHLORIDE(74817-54-2)

Safety Data

• Hazardous Substances Data: 74817-54-2(Hazardous Substances Data)

Usage

Uses

D-Glutamine Methyl Ester is labelled D-Glutamine (G597295). D-Glutamine is an unnatural isomer of L-Glutamine (G597000) that is present in human plasma an is a source of liberated ammonia. D-Glutamine can be synthesized by enzymatic means or can be found in cheeses, wine and vinegars as well. It is often used to determine the activity of Glutamine synthetase, an enzyme that is commonly found in the mammalian liver and brain that controls the use of nitrogen in cells.

InChI:InChI=1/C6H12N2O3.ClH/c1-11-6(10)4(7)2-3-5(8)9;/h4H,2-3,7H2,1H3,(H2,8,9);1H/t4-;/m1./s1

Upstream product

• 67-56-1 methanol 
• 56-85-9 L-glutamine 
• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 

Downstream Products

• 1372794-58-5 methyl 2-amino-5-[2-(3-benzoylphenyl)propanamido]-5-oxopentanoate 
• 865430-17-7 4-carbamoyl-2-(2-nitrobenzylamino)butyric acid methyl ester 
• 1053728-77-0 (S)-2-[((S)-2-{(S)-2-[Benzyloxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-tritylsulfanyl-propyl)-amino]-3-methyl-butyryl}-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl)-amino]-4-carbamoyl-butyric acid methyl ester 
• 110352-12-0 N-(benzyl-2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-D-glutamine methyl ester 
• 110314-94-8 N-(benzyl-2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-D-alanyl-D-glutamine methyl ester 
• 110314-95-9 N-(benzyl-2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-glycyl-D-glutamine methyl ester 
• 40847-06-1 N-L-Glutaminyl-γ-aminobuttersaeureethylester 
• 26199-61-1 Z-L-Phe-L-Gln-OMe 

Relevant articles and documents

Synthesis, molecular docking, and antiepileptic activity of new N-phthaloylglycine derivatives

Thalidomide (α-N-phthalimido-glutarimide), the withdrawn sedative compound, has recently been reemerged as a potent agent against epilepsy. In this study, five l-amino acid derivatives of N-phthaloylglycine were synthesized and were tested on pentylenetetrazole (PTZ) induced seizure mice model. N-phthaloylglycine was prepared by reaction of phthalic anhydride and glycine in the presence of triethylamine in toluene under reflux. Arginine, glutamine, leucine, phenylalanine, and tryptophan methyl ester were prepared and coupled with N-phthaloylglycine using coupling agents (EDC and HOBt). The final compounds were characterized by spectroscopic methods (1H NMR, 13 CNMR, IR, and MS). A docking study using AutoDock 4.2 was performed to predict the possible interactions of synthesized compounds on the GABAA receptor. All compounds were characterized, docked into the binding pocket of the GABAA receptor, and tested on pentylenetetrazole-induced seizures in mice. As expected, in silico studies demonstrated that all compounds interact efficiently with the GABAA receptor. All synthesized compounds showed satisfactory results leading to increased latency time to the first symptom of a seizure. The phenylalanine methyl ester derivative of N-phthaloylglycine (6d) had antiepileptic effects even more potent than thalidomide. Increasing lipophilicity and facilitating compounds delivery through l-amino acid carriers to the brain appear to be responsible for the remarkable activity of these compounds. Both in silico and in vivo results suggest that the l-amino acid derivatives of N-phthaloylglycine act as a novel compound against chemically induced seizures through interaction with the binding pocket of the GABAA receptor.

Heterocyclic inhibitors of farnesyl protein transferase

Inhibition of farnesyl protein transferase is effected by compounds of the formula its enantiomers, diastereomers, pharmaceutically acceptable salts, prodrugs or solvates thereof, wherein:, A1 and A2 are each independently H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, phenyl or substituted phenyl;, G1 is S or O;, G2 is H, -C(O)OH, -C(O)NH2, 5-tetrazolyl, -C(O)N(R7)OH or -CH2OH;, X is O or R8N;, Y and Z are each independently -CH2- or -C(O)-;, R1, R2, R3, R4, R5, R6 and R7 are each independently H or alkyl;, R1 may also be alkanoyl, R1 and A1 taken together may be -(CH2)m;, R8 is H, alkyl, phenyl, phenylalkyl, substituted phenyl, (substituted phenyl)alkyl or -C(O)R9;, R9 is H, alkyl, phenyl, phenylalkyl, substituted phenyl or (substituted phenyl)alkyl;, m is 3 or 4;, n is 0, 1 or 2;, p is 0, 1 or 2; and, q is 0 or 1, with the proviso that when p is 0, then q is also 0.