Organic Letters 2004-10-14

Asymmetric synthesis and translational competence of L-alpha-(1-cyclobutenyl)glycine.

Lasanthi P Jayathilaka, Mahua Deb, Robert F Standaert

Index: Org. Lett. 6(21) , 3659-62, (2004)

Full Text: HTML

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.

Related Compounds

  • 5-Hydroxylysine hy...

Related Articles:

Evaluation of the amino acid binding site of Mycobacterium tuberculosis glutamine synthetase for drug discovery.

2008-05-15

[Bioorg. Med. Chem. 16 , 5501-13, (2008)]

3-Hydroxylysine, a potential marker for studying radical-induced protein oxidation.

1998-11-01

[Chem. Res. Toxicol. 11 , 1265-1273, (1998)]

Free radical-mediated oxidation of free amino acids and amino acid residues in proteins.

2003-12-01

[Amino Acids 25 , 207-218, (2003)]

Characterization of acetyl-CoA: L-lysine N6-acetyltransferase, which catalyses the first step of carbon catabolism from lysine in Saccharomyces cerevisiae.

1993-01-01

[Arch. Microbiol. 160 , 397-400, (1993)]

[Change in the level of 1-aminochloropropane-1-carbonic acid. Activity of a protein inhibitor of polygalacturonase, intensity of formation of oligouronides in apples during ripening and treatment with haloethane derivatives and aminoethoxyvinylglycine].

2003-01-01

[Prikl. Biokhim. Mikrobiol. 39(4) , 461-4, (2003)]

More Articles...