Wybutosin

Structural formula
General
Surname	Wybutosin
other names	Y, yW (short code); (αS) -α - [(methoxycarbonyl) amino] -4,6-dimethyl-9-oxo-3-β- D -ribofuranosyl-4,9-dihydro-3H-imidazo [1,2- a ] purine-7 -butanoic acid methyl ester;
Molecular formula	C 21 H 28 N 6 O 9
External identifiers / databases
PubChem	90658156
Wikidata	Q1310878
properties
Molar mass	508.49 g mol −1
Physical state	firmly
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Wybutosine (Y, yW) is a rare nucleoside and occurs in the tRNA . It consists of β- D ribofuranose (sugar) and a heavily modified guanosine . It is a tricyclic nucleoside with a large side chain . It can be found as well as the Wyosin next to the anticodon at position 37 of most eukaryotic and archaeal phenylalanine -tRNAs. It was first isolated in 1968.

A tRNA ^Phe from S. cerevisiae .
Wybutosin is marked with a Y here .

literature

Taisuke Itaya, Tae Kanai, Takehiko Iida: Practical Synthesis of Wybutosine, the Hypermodified Nucleoside of Yeast Phenylalanine Transfer Ribonucleic Acid . In: Chemical & Pharmaceutical Bulletin . tape 50 , no. 4 , 2002, p. 530-533 , doi : 10.1248 / cpb.50.530 (English, jstage.jst.go.jp [PDF]).
Antje Hienzsch, Christian Deiml, Veronika Reiter, Thomas Carell : Total Synthesis of the Hypermodified RNA Bases Wybutosine and Hydroxywybutosine and Their Quantification Together with Other Modified RNA Bases in Plant Materials . In: Chemistry - A European Journal . tape 19 , no. 13 , March 25, 2013, p. 4244-4248 , doi : 10.1002 / chem . 201204209 , PMID 23417961 (English).

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Patrick A. Limbach, Pamela F. Crain, James A. McCloskey: "Summary: the modified nucleosides of RNA", Nucleic Acids Research , 1994 , 22 (12), pp. 2183-2196 ( doi: 10.1093 / nar / 22.12 .2183 , PMC 523672 (free full text), PMID 7518580 ).
↑ Akiko Noma, Yohei Kirino, Yoshiho Ikeuchi, Tsutomu Suzuki: “Biosynthesis of wybutosine, a hyper-modified nucleoside in eukaryotic phenylalanine tRNA”, The EMBO Journal , 2006 , 25 , pp. 2142-2154 ( doi: 10.1038 / sj.emboj .7601105 , PMC 1462984 (free full text, PDF), PMID 16642040 ).
↑ UL RajBhandary, RD Faulkner, Alexander Stuart: "Studies on polynucleotide: LXXIX. Yeast phenylalanine transfer ribonucleic acid: products obtained by degradation with pancreatic ribonuclease ", J. Biol. Chem. , 1968 , 243 , pp. 575-583 ( PMID 5637709 , PDF ).
↑ H. Shi, PB Moore : "The crystal structure of yeast phenylalanine tRNA at 1.93 Å resolution: a classic structure revisited", RNA , 2000 , 6 (8), pp. 1091-1105 ( PMC 1369984 (free full text), PMID 10943889 ).

Wybutosin's Modification Summary in the Modomics database, accessed January 13, 2014.