N-gamma-Glutamylglutamine

Base Information

• Chemical Name: N-gamma-Glutamylglutamine
• CAS No.: 10148-81-9
• Molecular Formula: C10H17 N3 O6
• Molecular Weight: 275.261
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID20394610
• Mol file: 10148-81-9.mol

Synonyms:N-gamma-Glutamylglutamine;(S)-2-Amino-5-(((S)-4-amino-1-carboxy-4-oxobutyl)amino)-5-oxopentanoic acid;2-amino-5-[(4-amino-1-carboxy-4-oxobutyl)amino]-5-oxopentanoic acid;SCHEMBL236265;DTXSID20394610;CHEBI:177278;FT-0772637

Chemical Property of N-gamma-Glutamylglutamine

Chemical Property:

• PSA: 172.81000
• LogP: -0.19510
• Storage Temp.: -15°C
• XLogP3: -4.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 275.11173527
• Heavy Atom Count: 19
• Complexity: 370

Purity/Quality:

98%,99%, ^*data from raw suppliers

H-γ-GLU-GLN-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(=O)NC(CCC(=O)N)C(=O)O)C(C(=O)O)N
• Uses: H-GAMMA-GLU-GLN-OH is an intestinal metabolite which may be related to myocardial infarction in rats.

Technology Process of N-gamma-Glutamylglutamine

There total 8 articles about N-gamma-Glutamylglutamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

benzyloxycarbonyl-α-benzyl-γ-L-glutamyl-L-glutamine (75898-61-2) → L-γ-glutamyl-L-glutamine (10148-81-9)

Guidance literature:

With hydrogen; palladium; In methanol; acetic acid; for 5h;

Reference yield: 36.4%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-glutamine (56-85-9,26700-71-0) → γ-L-glutamyl-L-valine (2746-34-1) + L-γ-glutamyl-L-glutamine (10148-81-9)

Guidance literature:

With sodium hydroxide; Escherichia coli K-12 SH642 γ-glutamyltranspeptidase; at 37 ℃; for 3h; pH=10;

DOI:10.1021/jf0347564

Reference yield:

L-glutamine (56-85-9,26700-71-0) + valylglycine (686-43-1,6491-60-7) → L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + L-γ-glutamyl-L-glutamine (10148-81-9) + C17H28N4O9 + γ-L-glutamyl-L-valylglycine

Guidance literature:

With γ-glutamyl transferase from Lid Loop B. subtilis; In aq. buffer; at 25 ℃; pH=8.5; Enzymatic reaction;

DOI:10.1039/c9ra05941e

upstream raw materials:

benzyloxycarbonyl-α-benzyl-γ-L-glutamyl-L-glutamine

L-valine

L-glutamine

Cbz-(L)-Glu-OBn

Downstream raw materials:

γ-L-glutamylisopropylamide

gamma-Glutamyl-glycyl-glycine

N-ethyl-L-glutamine

N-(γ-glutamyl)methylamine

Refernces

• 1、 Massone, Michela,Calvio, Cinzia,Rabuffetti, Marco,Speranza, Giovanna,Morelli, Carlo F.. "Effect of the inserted active-site-covering lid loop on the catalytic activity of a mutant: B. subtilis γ-glutamyltransferase (GGT)". . p. 34699 - 34709. Retrieved 2019.
• 2、 Imaoka, Masashi,Yano, Shigekazu,Okumura, Masashi,Hibi, Takao,Wakayama, Mamoru. "Molecular cloning and characterization of γ-Glutamyltranspeptidase from pseudomonas nitroreducens IFO12694". experimental part. p. 1936 - 1939. Retrieved 2011/06/11.