Wybutosine

Wybutosine
Names
	IUPAC name Methyl (2S)-4-(3,4″-dimethyl-3H-imidazo[1″,2″:1,2]inosin-5″-yl)-2-[(methoxycarbonyl)amino]butanoate
	Systematic IUPAC name Methyl (2S)-4-{3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6-dimethyl-9-oxo-4,9-dihydro-3H-imidazo[1,2-a]purin-7-yl}-2-[(methoxycarbonyl)amino]butanoate
	Other names 7-{(3S)-4-methoxy-3-[(methoxycarbonyl)amino]-4-oxobutyl}-4,6-dimethyl-3-(β-D-ribofuranosyl)-3,4-dihydro-9H-imidazo[1,2-a]purin-9-one (CHEBI); methyl 4-{3-[3,4-dihydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-yl]-4-methyl-6-methyl-8-oxo-1,3,4,5,7a-pentaaza-4,8-dihydro-3H-s-indacen-7-yl}-2-[methyl(oxycarbonylamino)]butanoate (ChemDoodle);
Identifiers
CAS Number	55196-46-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	yW
ChEBI	CHEBI:46574;
ChemSpider	28184605;
PubChem CID	14135916;
UNII	5PCY5AS87Q ;
CompTox Dashboard (EPA)	DTXSID401030490 ;
	InChI Key: QAOHCFGKCWTBGC-QHOAOGIMSA-N; InChI=1S/C21H28N6O9/c1-9-11(6-5-10(19(32)34-3)24-21(33)35-4)27-17(31)13-16(25(2)20(27)23-9)26(8-22-13)18-15(30)14(29)12(7-28)36-18/h8,10,12,14-15,18,28-30H,5-7H2,1-4H3,(H,24,33)/t10-,12+,14+,15+,18+/m0/s1;
	SMILES Cc1c(n2c(=O)c3c(n(c2n1)C)n(cn3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)CC[C@@H](C(=O)OC)NC(=O)OC;
Properties
Chemical formula	C21H28N6O9
Molar mass	508.488 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

In biochemistry, wybutosine (yW) is a heavily modified nucleoside of phenylalanine transfer RNA that stabilizes interactions between the codons and anti-codons during protein synthesis. Ensuring accurate synthesis of protein is essential in maintaining health as defects in tRNA modifications are able to cause disease. In eukaryotic organisms, it is found only in position 37, 3'-adjacent to the anticodon, of phenylalanine tRNA. Wybutosine enables correct translation through the stabilization of the codon-anticodon base pairing during the decoding process.