Synthesis of a fluorine-substituted puromycin derivative for Bronsted studies of ribosomal-catalyzed peptide bond formation

Article abstract of DOI:10.1021/jo802611t

The mechanism by which the ribosome catalyzes peptide bond formation remains controversial. Here we describe the synthesis of a nucleoside that can be used in Bronsted experiments to assess the transition state of ribosome catalyzed peptide bond formation. This substrate is the nucleoside 3 -amino-3 -deoxy-3 -[(3 R)-3-fluoro-L-phenyl-alanyl]-N⁶,N ⁶-dimethyladenosine, which was prepared from (1R,2R)-2-amino-1- phenylpropane-1,3-diol. This substrate is active in peptide bond formation on the ribosome and is a useful probe for Bronsted analysis experiments on the ribosome.