Ribosomal synthesis of dehydrobutyrine- and methyllanthionine-containing peptides.
We report here the ribosomal synthesis of methyllanthionine-containing cyclic peptides involving a site-specific incorporation of vinylglycine under the reprogrammed genetic code, followed by the isomerization of the vinylglycine to dehydrobutyrine, and the subsequent intramolecular Michael addition of a cysteine residue placed at a downstream position of the vinylglycine.
Goto
Yuki
Y
Research Center for Advanced Science and Technology, The University of Tokyo, 4-6-1, Komaba, Meguro, Tokyo 153-8904, Japan.
Iwasaki
Kazuhiro
K
Torikai
Kohei
K
Murakami
Hiroshi
H
Suga
Hiroaki
H
D000409:Alanine / Q000031:analogs & derivatives*; D000595:Amino Acid Sequence; D000613:Aminobutyrates; D001483:Base Sequence; D010456:Peptides, Cyclic / Q000096:biosynthesis* / Q000737:chemistry* / Q000235:genetics; D012333:RNA, Messenger / Q000235:genetics; D012270:Ribosomes / Q000378:metabolism*; D013440:Sulfides
D000613:Aminobutyrates; D010456:Peptides, Cyclic; D012333:RNA, Messenger; D013440:Sulfides; C088694:dehydrobutyrine; C005080:beta-methyllanthionine; D000409:Alanine