N-Acetylglutaminylglutamine amide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 597098

CAS#: 123199-99-5

Description: N-Acetylglutaminylglutamine amide is an an unusual dipeptide accumulated during osmotic stress in Rhizobium meliloti.


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N-Acetylglutaminylglutamine amide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597098
Name: N-Acetylglutaminylglutamine amide
CAS#: 123199-99-5
Chemical Formula: C12H21N5O5
Exact Mass: 315.1543
Molecular Weight: 315.33
Elemental Analysis: C, 45.71; H, 6.71; N, 22.21; O, 25.37


Synonym: N-Acetylglutaminylglutamine amide; NAGGN; N2-Acetyl-L-glutaminyl-L-glutamamide;

IUPAC/Chemical Name: (S)-2-acetamido-N1-((S)-1,5-diamino-1,5-dioxopentan-2-yl)pentanediamide

InChi Key: KLQXKYZBJWERSF-YUMQZZPRSA-N

InChi Code: InChI=1S/C12H21N5O5/c1-6(18)16-8(3-5-10(14)20)12(22)17-7(11(15)21)2-4-9(13)19/h7-8H,2-5H2,1H3,(H2,13,19)(H2,14,20)(H2,15,21)(H,16,18)(H,17,22)/t7-,8-/m0/s1

SMILES Code: O=C(N)CC[C@@H](C(N)=O)NC([C@H](CCC(N)=O)NC(C)=O)=O


Technical Data

Appearance:
Solid powder

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).

Harmonized System Code:
293490


References

1: Personius KE, Slusher BS, Udin SB. Neuromuscular NMDA Receptors Modulate Developmental Synapse Elimination. J Neurosci. 2016 Aug 24;36(34):8783-9. doi: 10.1523/JNEUROSCI.1181-16.2016. PubMed PMID: 27559162.

2: Freeman BC, Chen C, Yu X, Nielsen L, Peterson K, Beattie GA. Physiological and transcriptional responses to osmotic stress of two Pseudomonas syringae strains that differ in epiphytic fitness and osmotolerance. J Bacteriol. 2013 Oct;195(20):4742-52. doi: 10.1128/JB.00787-13. Epub 2013 Aug 16. PubMed PMID: 23955010; PubMed Central PMCID: PMC3807433.

3: Kurz M, Burch AY, Seip B, Lindow SE, Gross H. Genome-driven investigation of compatible solute biosynthesis pathways of Pseudomonas syringae pv. syringae and their contribution to water stress tolerance. Appl Environ Microbiol. 2010 Aug;76(16):5452-62. doi: 10.1128/AEM.00686-10. Epub 2010 Jun 25. PubMed PMID: 20581190; PubMed Central PMCID: PMC2918956.

4: Sagot B, Gaysinski M, Mehiri M, Guigonis JM, Le Rudulier D, Alloing G. Osmotically induced synthesis of the dipeptide N-acetylglutaminylglutamine amide is mediated by a new pathway conserved among bacteria. Proc Natl Acad Sci U S A. 2010 Jul 13;107(28):12652-7. doi: 10.1073/pnas.1003063107. Epub 2010 Jun 22. PubMed PMID: 20571117; PubMed Central PMCID: PMC2906558.

5: Bonaterra A, Cabrefiga J, Camps J, Montesinos E. Increasing survival and efficacy of a bacterial biocontrol agent of fire blight of rosaceous plants by means of osmoadaptation. FEMS Microbiol Ecol. 2007 Jul;61(1):185-95. Epub 2007 Mar 28. PubMed PMID: 17391328.

6: Talibart R, Jebbar M, Gouffi K, Pichereau V, Gouesbet G, Blanco C, Bernard T, Pocard J. Transient Accumulation of Glycine Betaine and Dynamics of Endogenous Osmolytes in Salt-Stressed Cultures of Sinorhizobium meliloti. Appl Environ Microbiol. 1997 Dec;63(12):4657-63. PubMed PMID: 16535748; PubMed Central PMCID: PMC1389304.

7: Mikkat S, Galinski EA, Berg G, Minkwitz A, Schoor A. Salt adaptation in pseudomonads: characterization of glucosylglycerol-synthesizing isolates from brackish coastal waters and the rhizosphere. Syst Appl Microbiol. 2000 Apr;23(1):31-40. PubMed PMID: 10879976.

8: Gouffi K, Bernard T, Blanco C. Osmoprotection by pipecolic acid in Sinorhizobium meliloti: specific effects of D and L isomers. Appl Environ Microbiol. 2000 Jun;66(6):2358-64. PubMed PMID: 10831411; PubMed Central PMCID: PMC110532.

9: Gouffi K, Blanco C. Is the accumulation of osmoprotectant the unique mechanism involved in bacterial osmoprotection? Int J Food Microbiol. 2000 Apr 10;55(1-3):171-4. PubMed PMID: 10791739.

10: Gouffi K, Pica N, Pichereau V, Blanco C. Disaccharides as a new class of nonaccumulated osmoprotectants for Sinorhizobium meliloti. Appl Environ Microbiol. 1999 Apr;65(4):1491-500. PubMed PMID: 10103242; PubMed Central PMCID: PMC91212.

11: Gouffi K, Pichereau V, Rolland JP, Thomas D, Bernard T, Blanco C. Sucrose is a nonaccumulated osmoprotectant in Sinorhizobium meliloti. J Bacteriol. 1998 Oct;180(19):5044-51. PubMed PMID: 9748435; PubMed Central PMCID: PMC107538.

12: Kets EP, Galinski EA, de Wit M, de Bont JA, Heipieper HJ. Mannitol, a novel bacterial compatible solute in Pseudomonas putida S12. J Bacteriol. 1996 Dec;178(23):6665-70. PubMed PMID: 8955280; PubMed Central PMCID: PMC178559.

13: Pocard JA, Smith LT, Smith GM, Le Rudulier D. A prominent role for glucosylglycerol in the adaptation of Pseudomonas mendocina SKB70 to osmotic stress. J Bacteriol. 1994 Nov;176(22):6877-84. PubMed PMID: 7961447; PubMed Central PMCID: PMC197056.

14: Talibart R, Jebbar M, Gouesbet G, Himdi-Kabbab S, Wróblewski H, Blanco C, Bernard T. Osmoadaptation in rhizobia: ectoine-induced salt tolerance. J Bacteriol. 1994 Sep;176(17):5210-7. PubMed PMID: 8071195; PubMed Central PMCID: PMC196703.

15: D'Souza-Ault MR, Smith LT, Smith GM. Roles of N-acetylglutaminylglutamine amide and glycine betaine in adaptation of Pseudomonas aeruginosa to osmotic stress. Appl Environ Microbiol. 1993 Feb;59(2):473-8. PubMed PMID: 8434912; PubMed Central PMCID: PMC202129.

16: Smith LT, Smith GM. An osmoregulated dipeptide in stressed Rhizobium meliloti. J Bacteriol. 1989 Sep;171(9):4714-7. PubMed PMID: 2768187; PubMed Central PMCID: PMC210271.