title: Characterization of the stereochemical configuration of lanthionines formed by the lanthipeptide synthetase GeoM.
abstract: The biosynthesis of the class II lanthipeptide geobacillin II was reconstituted in vitro. The purified precursor peptide was modified by the lanthipeptide synthetase GeoM at temperatures ranging between 37 and 80°C demonstrating the thermostability of the enzyme. Geobacillin II shares with cytolysin, haloduracin, and carnolysin a DhxDhxXxxXxxCys motif (Dhx = dehydroalanine or dehydrobutyrine) as precursor to its N-terminal A-ring. Like in these other three lantibiotics, the lanthionine in the A-ring of geobacillin II had the LL stereochemical configuration as shown by chiral gas chromatography/mass spectrometry. Various analogues of geobacillin II were produced using co-expression of mutants of the precursor peptide GeoAII and the synthetase GeoM in Escherichia coli. The findings in this study suggest that the stereochemical outcome of the A-ring in geobacillin II is not solely dependent on the peptide sequence as previously suggested for haloduracin © 2016 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 834-842, 2016.
authors.affiliation: Roger Adams Laboratory, Department of Biochemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801.
authors.forename: Neha
authors.initials: N
authors.lastname: Garg
authors.affiliation: Roger Adams Laboratory, Department of, Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Goto
authors.affiliation: College of Liberal Arts and Sciences, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801.
authors.forename: Ting
authors.initials: T
authors.lastname: Chen
authors.affiliation: Roger Adams Laboratory, Department of Biochemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801.|Roger Adams Laboratory, Department of, Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801.|Howard Hughes Medical Institute, 4000 Jones Bridge Road, Chevy Chase, MD 20815.
authors.forename: Wilfred A
authors.initials: WA
authors.lastname: van der Donk
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D001430:Bacteriocins / Q000096:biosynthesis / Q000737:chemistry; D004926:Escherichia coli / Q000201:enzymology; D010453:Peptide Synthases / Q000378:metabolism*; D013440:Sulfides / Q000737:chemistry / Q000378:metabolism
chemical_list: D001430:Bacteriocins; D013440:Sulfides; D010453:Peptide Synthases; C001520:lanthionine; D000409:Alanine
keywords: RiPP; antibiotics; lantibiotics; stereochemistry; thermophile