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Updated: Aug 21, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Asymmetric synthesis and translational competence of L-alpha-(1-cyclobutenyl)glycine
Lasanthi P Jayathilaka1, Mahua Deb, Robert F Standaert
1Department of Chemistry (M/C 111), University of Illinois at Chicago, 845 West Taylor Street, Room 4500 Chicago, Illinois 60607, USA.
Abstract:
[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.
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