Premium
Total Synthesis of the Hypermodified tRNA Nucleoside Epoxyqueuosine
Author(s) -
Thoma Ines,
Carell Thomas
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300586
Subject(s) - transfer rna , biosynthesis , nucleoside , chemistry , biochemistry , wobble base pair , stereochemistry , rna , gene
Queuosine is one of the most strongly modified nucleosides found in transferRNA (tRNA) of almost all species. Queuosine is found exclusively in the wooble position of the anticodon loop of several tRNA, where it is involved in tRNA Asp , tRNA Asn tRNA His , and tRNA Tyr . The biosynthesis of queuosine is performed by prokaryotes, and eukaryotes are fully dependent on this external source. To investigate the interesting biosynthesis of the Q base, we report here the first total synthesis of the direct biosynthetic precursor oQ. By using LC–MS in combination with special E. coli growing conditions (no vitamin B12 in the medium) we confirm the structure of the oQ natural products.