[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.
Amino acids U 0400Asymmetric Synthesis and Translational Competence of L-α-(1-Cyclobutenyl)glycine. -Title compound (I) is found to be a good substitute for isoleucine and valine (not for leucine) concerning the transport of green fluorescent protein in vitro. -(JAYATHILAKA, L. P.; DEB, M.; STANDAERT*, R. F.; Org. Lett. 6 (2004) 21, 3659-3662; Dep. Chem., Univ. Ill., Chicago, IL 60607, USA; Eng.) -Steudel 06-172
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