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MedKoo Cat#: 413805 | Name: Diphthamide

Description:

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

Diphthamide is a post-translationally modified histidine residue found in eukaryotic and archaeal translation elongation factor 2 (EF2). It is named after the fact that it is the target of diphtheria toxin (DT) produced by Corynebacterium diphtheriae.

Chemical Structure

Diphthamide
Diphthamide
CAS# 75645-22-6

Theoretical Analysis

MedKoo Cat#: 413805

Name: Diphthamide

CAS#: 75645-22-6

Chemical Formula: C13H23N5O3

Exact Mass: 297.1801

Molecular Weight: 297.36

Elemental Analysis: C, 52.51; H, 7.80; N, 23.55; O, 16.14

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Diphthamide
IUPAC/Chemical Name
1H-Imidazole-2-propanaminium, alpha-(aminocarbonyl)-4-(2-amino-2-carboxyethyl)-N,N,N-trimethyl-, hydroxide, inner salt
InChi Key
FOOBQHKMWYGHCE-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21)
SMILES Code
C[N+](C)(C)C(C(N)=O)CCC1=NC(CC(N)C([O-])=O)=CN1
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 297.36 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.

Recalculate based on batch purity %
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: Hawer H, Mendelsohn BA, Mayer K, Kung A, Malhotra A, Tuupanen S, Schleit J, Brinkmann U, Schaffrath R. Diphthamide-deficiency syndrome: a novel human developmental disorder and ribosomopathy. Eur J Hum Genet. 2020 Nov;28(11):1497-1508. doi: 10.1038/s41431-020-0668-y. Epub 2020 Jun 23. PMID: 32576952; PMCID: PMC7575589. 2: Togami K, Pastika T, Stephansky J, Ghandi M, Christie AL, Jones KL, Johnson CA, Lindsay RW, Brooks CL, Letai A, Craig JW, Pozdnyakova O, Weinstock DM, Montero J, Aster JC, Johannessen CM, Lane AA. DNA methyltransferase inhibition overcomes diphthamide pathway deficiencies underlying CD123-targeted treatment resistance. J Clin Invest. 2019 Nov 1;129(11):5005-5019. doi: 10.1172/JCI128571. PMID: 31437130; PMCID: PMC6819120. 3: Schaffrath R, Abdel-Fattah W, Klassen R, Stark MJ. The diphthamide modification pathway from Saccharomyces cerevisiae--revisited. Mol Microbiol. 2014 Dec;94(6):1213-26. doi: 10.1111/mmi.12845. Epub 2014 Nov 17. PMID: 25352115. 4: Tsuda-Sakurai K, Miura M. The hidden nature of protein translational control by diphthamide: the secrets under the leather. J Biochem. 2019 Jan 1;165(1):1-8. doi: 10.1093/jb/mvy071. PMID: 30204891. 5: Mayer K, Mundigl O, Kettenberger H, Birzele F, Stahl S, Pastan I, Brinkmann U. Diphthamide affects selenoprotein expression: Diphthamide deficiency reduces selenocysteine incorporation, decreases selenite sensitivity and pre-disposes to oxidative stress. Redox Biol. 2019 Jan;20:146-156. doi: 10.1016/j.redox.2018.09.015. Epub 2018 Sep 26. PMID: 30312900; PMCID: PMC6180344. 6: Su X, Lin Z, Lin H. The biosynthesis and biological function of diphthamide. Crit Rev Biochem Mol Biol. 2013 Nov-Dec;48(6):515-21. doi: 10.3109/10409238.2013.831023. Epub 2013 Aug 23. PMID: 23971743; PMCID: PMC4280834. 7: Hawer H, Ütkür K, Arend M, Mayer K, Adrian L, Brinkmann U, Schaffrath R. Importance of diphthamide modified EF2 for translational accuracy and competitive cell growth in yeast. PLoS One. 2018 Oct 18;13(10):e0205870. doi: 10.1371/journal.pone.0205870. PMID: 30335802; PMCID: PMC6193676. 8: Liu J, Zuo Z, Zou M, Finkel T, Liu S. Identification of the transcription factor Miz1 as an essential regulator of diphthamide biosynthesis using a CRISPR-mediated genome-wide screen. PLoS Genet. 2020 Oct 15;16(10):e1009068. doi: 10.1371/journal.pgen.1009068. PMID: 33057331; PMCID: PMC7591051. 9: Tsuda-Sakurai K, Kimura M, Miura M. Diphthamide modification of eEF2 is required for gut tumor-like hyperplasia induced by oncogenic Ras. Genes Cells. 2020 Feb;25(2):76-85. doi: 10.1111/gtc.12742. Epub 2020 Jan 5. PMID: 31828897. 10: Dong M, Dando EE, Kotliar I, Su X, Dzikovski B, Freed JH, Lin H. The asymmetric function of Dph1-Dph2 heterodimer in diphthamide biosynthesis. J Biol Inorg Chem. 2019 Sep;24(6):777-782. doi: 10.1007/s00775-019-01702-0. Epub 2019 Aug 28. PMID: 31463593; PMCID: PMC6893874.