title: Artificial lantipeptides from in vitro translations.
abstract: We have devised a protocol for enzyme-free insertion of dehydroalanine, dehydrobutyrine and thioether crosslinks into translated peptides. In vitro translation using 4-selenalysine and 4-selenoisoleucine as substitutes for lysine and isoleucine yields peptides that can be converted to polycyclic structures using mild chemistry in water. This methodology presents a gateway for exploring the potential of artificial lantipeptides as scaffolds for drug development.
authors.affiliation: Howard Hughes Medical Institute and Center for Computational and Integrative Biology, Massachusetts General Hospital, 185 Cambridge St., Boston, USA.
authors.forename: Florian P
authors.initials: FP
authors.lastname: Seebeck
authors.forename: Alonso
authors.initials: A
authors.lastname: Ricardo
authors.forename: Jack W
authors.initials: JW
authors.lastname: Szostak
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000595:Amino Acid Sequence; D000613:Aminobutyrates / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D008969:Molecular Sequence Data; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D010452:Peptide Biosynthesis; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013440:Sulfides / Q000737:chemistry*
chemical_list: D000613:Aminobutyrates; D003432:Cross-Linking Reagents; D016566:Organoselenium Compounds; D010455:Peptides; D013440:Sulfides; C088694:dehydrobutyrine; C011351:selenalysine; C015102:dehydroalanine; D008239:Lysine; D000409:Alanine