MedKoo Cat#: 341060 | Name: Wyosine

Description:

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

Wyosine is a biochemical.

Chemical Structure

Wyosine
Wyosine
CAS#52662-10-9

Theoretical Analysis

MedKoo Cat#: 341060

Name: Wyosine

CAS#: 52662-10-9

Chemical Formula: C14H17N5O5

Exact Mass: 335.1230

Molecular Weight: 335.32

Elemental Analysis: C, 50.15; H, 5.11; N, 20.89; O, 23.86

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
Wyosine
IUPAC/Chemical Name
9H-Imidazo(1,2-a)purin-9-one, 3,4-dihydro-4,6-dimethyl-3-beta-D-ribofuranosyl-
InChi Key
JCZSFCLRSONYLH-QYVSTXNMSA-N
InChi Code
InChI=1S/C14H17N5O5/c1-6-3-18-12(23)8-11(17(2)14(18)16-6)19(5-15-8)13-10(22)9(21)7(4-20)24-13/h3,5,7,9-10,13,20-22H,4H2,1-2H3/t7-,9-,10-,13-/m1/s1
SMILES Code
n1cn(c2n(c3n(c(c12)=O)cc(n3)C)C)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 335.32 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: Wang C, Jia Q, Zeng J, Chen R, Xie W. Structural insight into the methyltransfer mechanism of the bifunctional Trm5. Sci Adv. 2017 Dec 1;3(12):e1700195. doi: 10.1126/sciadv.1700195. eCollection 2017 Dec. PubMed PMID: 29214216; PubMed Central PMCID: PMC5714064. 2: Fandilolu PM, Kamble AS, Sambhare SB, Sonawane KD. Conformational preferences and structural analysis of hypermodified nucleoside, peroxywybutosine (o2yW) found at 37(th) position in anticodon loop of tRNA(Phe) and its role in modulating UUC codon-anticodon interactions. Gene. 2018 Jan 30;641:310-325. doi: 10.1016/j.gene.2017.10.072. Epub 2017 Oct 26. PubMed PMID: 29107006. 3: Wu J, Jia Q, Wu S, Zeng H, Sun Y, Wang C, Ge R, Xie W. The crystal structure of the Pyrococcus abyssi mono-functional methyltransferase PaTrm5b. Biochem Biophys Res Commun. 2017 Nov 4;493(1):240-245. doi: 10.1016/j.bbrc.2017.09.038. Epub 2017 Sep 11. PubMed PMID: 28911863. 4: Urbonavičius J, Rutkienė R, Lopato A, Tauraitė D, Stankevičiūtė J, Aučynaitė A, Kaliniene L, van Tilbeurgh H, Meškys R. Evolution of tRNAPhe:imG2 methyltransferases involved in the biosynthesis of wyosine derivatives in Archaea. RNA. 2016 Dec;22(12):1871-1883. Epub 2016 Oct 20. PubMed PMID: 27852927; PubMed Central PMCID: PMC5113207. 5: Wang C, Jia Q, Chen R, Wei Y, Li J, Ma J, Xie W. Crystal structures of the bifunctional tRNA methyltransferase Trm5a. Sci Rep. 2016 Sep 15;6:33553. doi: 10.1038/srep33553. PubMed PMID: 27629654; PubMed Central PMCID: PMC5024318. 6: Jahnz-Wechmann Z, Framski GR, Januszczyk PA, Boryski J. Base-Modified Nucleosides: Etheno Derivatives. Front Chem. 2016 Apr 28;4:19. doi: 10.3389/fchem.2016.00019. eCollection 2016. Review. PubMed PMID: 27200341; PubMed Central PMCID: PMC4848297. 7: Sample PJ, Kořený L, Paris Z, Gaston KW, Rubio MA, Fleming IM, Hinger S, Horáková E, Limbach PA, Lukeš J, Alfonzo JD. A common tRNA modification at an unusual location: the discovery of wyosine biosynthesis in mitochondria. Nucleic Acids Res. 2015 Apr 30;43(8):4262-73. doi: 10.1093/nar/gkv286. Epub 2015 Apr 6. PubMed PMID: 25845597; PubMed Central PMCID: PMC4417183. 8: Urbonavičius J, Meškys R, Grosjean H. Biosynthesis of wyosine derivatives in tRNA(Phe) of Archaea: role of a remarkable bifunctional tRNA(Phe):m1G/imG2 methyltransferase. RNA. 2014 Jun;20(6):747-53. doi: 10.1261/rna.043315.113. Review. PubMed PMID: 24837075; PubMed Central PMCID: PMC4024628. 9: Young AP, Bandarian V. Radical mediated ring formation in the biosynthesis of the hypermodified tRNA base wybutosine. Curr Opin Chem Biol. 2013 Aug;17(4):613-8. doi: 10.1016/j.cbpa.2013.05.035. Epub 2013 Jul 12. Review. PubMed PMID: 23856057; PubMed Central PMCID: PMC4320972. 10: Baranowski D, Golankiewicz B, Folkman W, Popenda M. 2-Methylwyosine, a nucleoside with restricted anti conformation in the east region enforced by nucleobase moiety modification: synthesis and conformational analysis by NMR and molecular dynamics. Nucleosides Nucleotides Nucleic Acids. 2012;31(10):707-19. doi: 10.1080/15257770.2012.724133. PubMed PMID: 23067123. 11: Perche-Letuvée P, Kathirvelu V, Berggren G, Clemancey M, Latour JM, Maurel V, Douki T, Armengaud J, Mulliez E, Fontecave M, Garcia-Serres R, Gambarelli S, Atta M. 4-Demethylwyosine synthase from Pyrococcus abyssi is a radical-S-adenosyl-L-methionine enzyme with an additional [4Fe-4S](+2) cluster that interacts with the pyruvate co-substrate. J Biol Chem. 2012 Nov 30;287(49):41174-85. doi: 10.1074/jbc.M112.405019. Epub 2012 Oct 5. PubMed PMID: 23043105; PubMed Central PMCID: PMC3510817. 12: de Crécy-Lagard V, Brochier-Armanet C, Urbonavicius J, Fernandez B, Phillips G, Lyons B, Noma A, Alvarez S, Droogmans L, Armengaud J, Grosjean H. Biosynthesis of wyosine derivatives in tRNA: an ancient and highly diverse pathway in Archaea. Mol Biol Evol. 2010 Sep;27(9):2062-77. doi: 10.1093/molbev/msq096. Epub 2010 Apr 9. PubMed PMID: 20382657; PubMed Central PMCID: PMC4481705. 13: Suzuki Y, Noma A, Suzuki T, Senda M, Senda T, Ishitani R, Nureki O. Crystal structure of the radical SAM enzyme catalyzing tricyclic modified base formation in tRNA. J Mol Biol. 2007 Oct 5;372(5):1204-14. Epub 2007 Jul 26. PubMed PMID: 17727881. 14: Waas WF, Druzina Z, Hanan M, Schimmel P. Role of a tRNA base modification and its precursors in frameshifting in eukaryotes. J Biol Chem. 2007 Sep 7;282(36):26026-34. Epub 2007 Jul 9. PubMed PMID: 17623669. 15: Waas WF, de Crécy-Lagard V, Schimmel P. Discovery of a gene family critical to wyosine base formation in a subset of phenylalanine-specific transfer RNAs. J Biol Chem. 2005 Nov 11;280(45):37616-22. Epub 2005 Sep 13. PubMed PMID: 16162496. 16: Baranowski D, Golankiewicz B, Plavec J. Conformationally restricted 2-substituted wyosine derivatives. 1H, 13C, and 15N NMR study. Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1669-72. PubMed PMID: 14565491. 17: Baranowski D, Golankiewicz B, Plavec J. Conformationally constrained tricyclic nucleosides. Role of electronic and steric factors. Nucleic Acids Res Suppl. 2003;(3):99-100. PubMed PMID: 14510399. 18: Itaya T, Kanai T, Sawada T. Structure of wyosine, the condensed tricyclic nucleoside of torula yeast phenylalanine transfer ribonucleic acid. Chem Pharm Bull (Tokyo). 2002 Apr;50(4):547-8. PubMed PMID: 11964008. 19: McCloskey JA, Graham DE, Zhou S, Crain PF, Ibba M, Konisky J, Söll D, Olsen GJ. Post-transcriptional modification in archaeal tRNAs: identities and phylogenetic relations of nucleotides from mesophilic and hyperthermophilic Methanococcales. Nucleic Acids Res. 2001 Nov 15;29(22):4699-706. PubMed PMID: 11713320; PubMed Central PMCID: PMC92529. 20: Golankiewicz B. Synthetic and biological applications of tricyclic analogues of guanosine. Acta Biochim Pol. 1996;43(1):53-64. Review. PubMed PMID: 8790712.