790244-67-6Relevant academic research and scientific papers
Asymmetric synthesis and translational competence of L-α-(1- Cyclobutenyl)glycine
Jayathilaka, Lasanthi P.,Deb, Mahua,Standaert, Robert F.
, p. 3659 - 3662 (2004)
(Chemical Equation Presented) L-α-(1-Cyclobutenyl)glycine (1-Cbg) was targeted as a potentially translatable analogue of isoleucine and valine and as a useful building block for peptides. An enantioselective synthesis was executed in which the key step was diastereoselective addition of 1-cyclobutenylmagnesium bromide to the sulfinimine 2b derived from (S)-t-butanesulfinimide and tert-butyl glyoxylate. 1-Cbg was found to substitute efficiently for isoleucine and valine, but not leucine, in the translation of green fluorescent protein in vitro.
