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MedKoo Cat#: 463778 | Name: DHU
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Description:

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

5,6-Dihydrouridine (DHU) is a pyrimidine nucleoside and derivative of uridine. It is present in, and provides conformational flexibility to, tRNA from bacteria, eukaryotes, and some archaea. 5,6-Dihydrouridine inhibits E. coli cytidine deaminase in a cell-free assay. Serum levels of 5,6-dihydrouridine are increased in patients with prostate cancer and positively correlated with lethality.

Chemical Structure

DHU
CAS#5627-05-4

Theoretical Analysis

MedKoo Cat#: 463778

Name: DHU

CAS#: 5627-05-4

Chemical Formula: C9H14N2O6

Exact Mass: 246.0852

Molecular Weight: 246.22

Elemental Analysis: C, 43.90; H, 5.73; N, 11.38; O, 38.99

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
500mg USD 550.00 2 Weeks
1g USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
DHU; 5,6-Dihydrouridine; 5,6 Dihydrouridine;
IUPAC/Chemical Name
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)dihydropyrimidine-2,4(1H,3H)-dione
InChi Key
ZPTBLXKRQACLCR-XVFCMESISA-N
InChi Code
InChI=1S/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
SMILES Code
O[C@H]1[C@@]([H])(O[C@H](CO)[C@H]1O)N2C(NC(CC2)=O)=O
Appearance
Solid powder
Purity
>95% (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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 246.22 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: Bulygin AA, Kuznetsova AA, Vorobjev YN, Fedorova OS, A Kuznetsov N. The Role of Active-Site Plasticity in Damaged-Nucleotide Recognition by Human Apurinic/Apyrimidinic Endonuclease APE1. Molecules. 2020 Aug 28;25(17):3940. doi: 10.3390/molecules25173940. PMID: 32872297; PMCID: PMC7504742. 2: Alekseeva IV, Kuznetsova AA, Bakman AS, Fedorova OS, Kuznetsov NA. The role of active-site amino acid residues in the cleavage of DNA and RNA substrates by human apurinic/apyrimidinic endonuclease APE1. Biochim Biophys Acta Gen Subj. 2020 Dec;1864(12):129718. doi: 10.1016/j.bbagen.2020.129718. Epub 2020 Aug 25. PMID: 32858086. 3: Yanas A, Liu KF. RNA modifications and the link to human disease. Methods Enzymol. 2019;626:133-146. doi: 10.1016/bs.mie.2019.08.003. Epub 2019 Sep 3. PMID: 31606073. 4: Kladova OA, Kuznetsov NA, Fedorova OS. Thermodynamics of the DNA Repair Process by Endonuclease VIII. Acta Naturae. 2019 Jan-Mar;11(1):29-37. PMID: 31024746; PMCID: PMC6475869. 5: Kuznetsova AA, Matveeva AG, Milov AD, Vorobjev YN, Dzuba SA, Fedorova OS, Kuznetsov NA. Substrate specificity of human apurinic/apyrimidinic endonuclease APE1 in the nucleotide incision repair pathway. Nucleic Acids Res. 2018 Nov 30;46(21):11454-11465. doi: 10.1093/nar/gky912. PMID: 30329131; PMCID: PMC6265485. 6: Bou-Nader C, Montémont H, Guérineau V, Jean-Jean O, Brégeon D, Hamdane D. Unveiling structural and functional divergences of bacterial tRNA dihydrouridine synthases: perspectives on the evolution scenario. Nucleic Acids Res. 2018 Feb 16;46(3):1386-1394. doi: 10.1093/nar/gkx1294. PMID: 29294097; PMCID: PMC5814906. 7: Sridharan G, Ramani P, Patankar S. Serum metabolomics in oral leukoplakia and oral squamous cell carcinoma. J Cancer Res Ther. 2017 Jul-Sep;13(3):556-561. doi: 10.4103/jcrt.JCRT_1233_16. PMID: 28862226. 8: Akishev Z, Taipakova S, Joldybayeva B, Zutterling C, Smekenov I, Ishchenko AA, Zharkov DO, Bissenbaev AK, Saparbaev M. The major Arabidopsis thaliana apurinic/apyrimidinic endonuclease, ARP is involved in the plant nucleotide incision repair pathway. DNA Repair (Amst). 2016 Dec;48:30-42. doi: 10.1016/j.dnarep.2016.10.009. Epub 2016 Oct 29. PMID: 27836324. 9: Timofeyeva NA, Fedorova OS. A kinetic mechanism of repair of DNA containing α-anomeric deoxyadenosine by human apurinic/apyrimidinic endonuclease 1. Mol Biosyst. 2016 Oct 18;12(11):3435-3446. doi: 10.1039/c6mb00511j. PMID: 27722620. 10: Millar D, Christova Y, Holliger P. A polymerase engineered for bisulfite sequencing. Nucleic Acids Res. 2015 Dec 15;43(22):e155. doi: 10.1093/nar/gkv798. Epub 2015 Aug 13. PMID: 26271989; PMCID: PMC4678845. 11: Kusuba H, Yoshida T, Iwasaki E, Awai T, Kazayama A, Hirata A, Tomikawa C, Yamagami R, Hori H. In vitro dihydrouridine formation by tRNA dihydrouridine synthase from Thermus thermophilus, an extreme-thermophilic eubacterium. J Biochem. 2015 Dec;158(6):513-21. doi: 10.1093/jb/mvv066. Epub 2015 Jun 24. PMID: 26112661. 12: Treptow TG, Figueiró F, Jandrey EH, Battastini AM, Salbego CG, Hoppe JB, Taborda PS, Rosa SB, Piovesan LA, Montes D'Oca Cda R, Russowsky D, Montes D'Oca MG. Novel hybrid DHPM-fatty acids: synthesis and activity against glioma cell growth in vitro. Eur J Med Chem. 2015 May 5;95:552-62. doi: 10.1016/j.ejmech.2015.03.062. Epub 2015 Mar 28. PMID: 25863023. 13: Kuznetsova AA, Kuznetsov NA, Vorobjev YN, Barthes NP, Michel BY, Burger A, Fedorova OS. New environment-sensitive multichannel DNA fluorescent label for investigation of the protein-DNA interactions. PLoS One. 2014 Jun 12;9(6):e100007. doi: 10.1371/journal.pone.0100007. PMID: 24925085; PMCID: PMC4055743. 14: Krog JS, Español Y, Giessing AM, Dziergowska A, Malkiewicz A, Ribas de Pouplana L, Kirpekar F. 3-(3-amino-3-carboxypropyl)-5,6-dihydrouridine is one of two novel post-transcriptional modifications in tRNALys(UUU) from Trypanosoma brucei. FEBS J. 2011 Dec;278(24):4782-96. doi: 10.1111/j.1742-4658.2011.08379.x. Epub 2011 Oct 28. PMID: 22040320. 15: Timofeyeva NA, Koval VV, Ishchenko AA, Saparbaev MK, Fedorova OS. Lys98 substitution in human AP endonuclease 1 affects the kinetic mechanism of enzyme action in base excision and nucleotide incision repair pathways. PLoS One. 2011;6(9):e24063. doi: 10.1371/journal.pone.0024063. Epub 2011 Sep 1. PMID: 21912662; PMCID: PMC3164677. 16: Newman CA, Resendiz MJ, Sczepanski JT, Greenberg MM. Photochemical generation and reactivity of the 5,6-dihydrouridin-6-yl radical. J Org Chem. 2009 Sep 18;74(18):7007-12. doi: 10.1021/jo9012805. PMID: 19691299. 17: Nawrot B, Sochacka E. Preparation of short interfering RNA containing the modified nucleosides 2-thiouridine, pseudouridine, or dihydrouridine. Curr Protoc Nucleic Acid Chem. 2009 Jun;Chapter 16:Unit 16.2. doi: 10.1002/0471142700.nc1602s37. PMID: 19488969. 18: Watanabe H, Tokiwano T, Oikawa H. Biosynthetic study of FR-900848: origin of the aminodeoxynucleoside part. J Antibiot (Tokyo). 2006 Sep;59(9):607-10. doi: 10.1038/ja.2006.82. PMID: 17136894. 19: Savage DF, de Crécy-Lagard V, Bishop AC. Molecular determinants of dihydrouridine synthase activity. FEBS Lett. 2006 Oct 2;580(22):5198-202. doi: 10.1016/j.febslet.2006.08.062. Epub 2006 Sep 5. PMID: 16962594. 20: Cardaioli E, Da Pozzo P, Radi E, Dotti MT, Federico A. A novel heteroplasmic tRNA(Leu(CUN)) mtDNA point mutation associated with chronic progressive external ophthalmoplegia. Biochem Biophys Res Commun. 2005 Feb 18;327(3):675-8. doi: 10.1016/j.bbrc.2004.11.170. PMID: 15649400.