title: The dynamic structure of jadomycin B and the amino acid incorporation step of its biosynthesis.
abstract: Jadomycin B, an antifungal antibiotic with a unique 8H-benz[b]oxazolo[3,2-f]phenanthridine pentacyclic skeleton produced by the bacterium Streptomyces venezuelae ISP 5230, exists in a dynamic equilibrium of two diastereomers differing in the configuration of C-3a. Several novel jadomycins with various amino acid-derived 1-side chains could be generated, by replacing isoleucine in the production medium of S. venezuelae with other amino acids. These two findings led to the conclusion that a nonenzymatic reaction with the amino acid followed by a likewise nonenzymatic cyclization cascade are crucial for its late biosynthesis.
authors.affiliation: Division of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, 907 Rose Street, Lexington, Kentucky 40536-0082, USA.
authors.forename: Uwe
authors.initials: U
authors.lastname: Rix
authors.forename: Jianting
authors.initials: J
authors.lastname: Zheng
authors.forename: Lily L
authors.initials: LL
authors.lastname: Remsing Rix
authors.forename: Lisa
authors.initials: L
authors.lastname: Greenwell
authors.forename: Keqian
authors.initials: K
authors.lastname: Yang
authors.forename: Jürgen
authors.initials: J
authors.lastname: Rohr
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism*; D006860:Hydrogen Bonding; D007532:Isoleucine / Q000737:chemistry / Q000378:metabolism; D007546:Isoquinolines / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007546:Isoquinolines; D007532:Isoleucine; C081750:jadomycin B