Asymmetric synthesis and translational competence of L-alpha-(1-cyclobutenyl)glycine.
[reaction: see text] L-alpha-(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.
Jayathilaka
Lasanthi P
LP
Department of Chemistry (M/C 111), University of Illinois at Chicago, 845 West Taylor Street, Room 4500 Chicago, Illinois 60607, USA.
Deb
Mahua
M
Standaert
Robert F
RF
D000613:Aminobutyrates / Q000138:chemical synthesis* / Q000494:pharmacology; D049452:Green Fluorescent Proteins / Q000235:genetics; D014176:Protein Biosynthesis / Q000187:drug effects*; D013237:Stereoisomerism
D000613:Aminobutyrates; D049452:Green Fluorescent Proteins; C012175:2-amino-4-(2-aminoethoxy)butanoic acid