Synthesis of a fluorine-substituted puromycin derivative for Brønsted studies of ribosomal-catalyzed peptide bond formation.
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 Brønsted 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]-N(6),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 Brønsted analysis experiments on the ribosome.
Okuda
Kensuke
K
Gifu Pharmaceutical University, Gifu 502-8585, Japan. okuda@gifu-pu.ac.jp
Hirota
Takashi
T
Kingery
David A
DA
Nagasawa
Hideko
H
D002384:Catalysis; D005461:Fluorine; D010455:Peptides / Q000138:chemical synthesis*; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D012270:Ribosomes
D010455:Peptides; D005461:Fluorine; D011691:Puromycin