Synonym
Glutathione amide; GASH cpd; L-gamma-Glutamyl-L-cysteinylglycinamide;
IUPAC/Chemical Name
N5-((R)-1-((2-amino-2-oxoethyl)amino)-3-mercapto-1-oxopropan-2-yl)-L-glutamine
InChi Key
FBCIXVYKFFJYFT-WDSKDSINSA-N
InChi Code
InChI=1S/C10H18N4O5S/c11-5(10(18)19)1-2-8(16)14-6(4-20)9(17)13-3-7(12)15/h5-6,20H,1-4,11H2,(H2,12,15)(H,13,17)(H,14,16)(H,18,19)/t5-,6-/m0/s1
SMILES Code
O=C(N)CNC([C@H](CS)NC(CC[C@@H](C(O)=O)N)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
306.33
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Van Petegem F, De Vos D, Savvides S, Vergauwen B, Van Beeumen J. Understanding nicotinamide dinucleotide cofactor and substrate specificity in class I flavoprotein disulfide oxidoreductases: crystallographic analysis of a glutathione amide reductase. J Mol Biol. 2007 Dec 7;374(4):883-9. Epub 2007 Sep 29. PubMed PMID: 17977556.
2: Vergauwen B, Pauwels F, Vaneechoutte M, Van Beeumen JJ. Exogenous glutathione completes the defense against oxidative stress in Haemophilus influenzae. J Bacteriol. 2003 Mar;185(5):1572-81. PubMed PMID: 12591874; PubMed Central PMCID: PMC148052.
3: Vergauwen B, Van Petegem F, Remaut H, Pauwels F, Van Beeumen JJ. Crystallization and preliminary X-ray crystallographic analysis of glutathione amide reductase from Chromatium gracile. Acta Crystallogr D Biol Crystallogr. 2002 Feb;58(Pt 2):339-40. Epub 2002 Jan 24. PubMed PMID: 11807270.
4: Fahey RC. Novel thiols of prokaryotes. Annu Rev Microbiol. 2001;55:333-56. Review. PubMed PMID: 11544359.
5: Vergauwen B, Pauwels F, Jacquemotte F, Meyer TE, Cusanovich MA, Bartsch RG, Van Beeumen JJ. Characterization of glutathione amide reductase from Chromatium gracile. Identification of a novel thiol peroxidase (Prx/Grx) fueled by glutathione amide redox cycling. J Biol Chem. 2001 Jun 15;276(24):20890-7. Epub 2001 Apr 3. PubMed PMID: 11399772.
6: Kwon DS, Lin CH, Chen S, Coward JK, Walsh CT, Bollinger JM Jr. Dissection of glutathionylspermidine synthetase/amidase from Escherichia coli into autonomously folding and functional synthetase and amidase domains. J Biol Chem. 1997 Jan 24;272(4):2429-36. PubMed PMID: 8999955.
7: Bartsch RG, Newton GL, Sherrill C, Fahey RC. Glutathione amide and its perthiol in anaerobic sulfur bacteria. J Bacteriol. 1996 Aug;178(15):4742-6. PubMed PMID: 8755912; PubMed Central PMCID: PMC178251.
