Synthesis of the Transfer-RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate

摘要

Transfer RNAs (tRNAs) are key molecules needed for the decoding of the genetic information at the ribosome. The tRNAs contain the four canonical RNA bases plus a large set of modified nucleotides whose function in the tRNA charging and decoding process is largely unknown. Queuosine (Q; 1) and its galactosylated, mannosylated, or amino acid modified derivatives (Scheme 1) are important hypermodified RNA bases present in the anticodon stem loop of various tRNAs. It is currently hypothesized that these base derivatives are needed to fine-regulate the translational process.