title: Ribosylhopane, a novel bacterial hopanoid, as precursor of C35 bacteriohopanepolyols in Streptomyces coelicolor A3(2).
abstract: Wild-type Streptomyces coelicolor A3(2) produces aminobacteriohopanetriol as the only elongated C35 hopanoid. The hopanoid phenotype of two mutants bearing a deletion of genes from a previously identified hopanoid biosynthesis gene cluster provides clues to the formation of C35 bacteriohopanepolyols. orf14 encodes a putative nucleosidase; its deletion induces the accumulation of adenosylhopane as it cannot be converted into ribosylhopane. orf18 encodes a putative transaminase; its deletion results in the accumulation of adenosylhopane, ribosylhopane, and bacteriohopanetetrol. Ribosylhopane was postulated twenty years ago as a precursor for bacterial hopanoids but was never identified in a bacterium. Absence of the transaminase encoded by orf18 prevents the reductive amination of ribosylhopane into aminobacteriohopanetriol and induces its accumulation. Its reduction by an aldose-reductase-like enzyme produces bacteriohopanetetrol, which is normally not present in S. coelicolor.
authors.affiliation: Université de Strasbourg/CNRS, Institut Le Bel, 4 rue Blaise Pascal, 67070 Strasbourg, Cedex (France).
authors.forename: Wenjun
authors.initials: W
authors.lastname: Liu
authors.forename: Elias
authors.initials: E
authors.lastname: Sakr
authors.forename: Philippe
authors.initials: P
authors.lastname: Schaeffer
authors.forename: Helen M
authors.initials: HM
authors.lastname: Talbot
authors.forename: Janina
authors.initials: J
authors.lastname: Donisi
authors.forename: Thomas
authors.initials: T
authors.lastname: Härtner
authors.forename: Elmar
authors.initials: E
authors.lastname: Kannenberg
authors.forename: Eriko
authors.initials: E
authors.lastname: Takano
authors.forename: Michel
authors.initials: M
authors.lastname: Rohmer
mesh_terms: D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism; D053898:Biosynthetic Pathways; D017353:Gene Deletion; D005798:Genes, Bacterial; D005810:Multigene Family; D009699:N-Glycosyl Hydrolases / Q000235:genetics / Q000378:metabolism; D048372:Streptomyces coelicolor / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D000637:Transaminases / Q000235:genetics / Q000378:metabolism; D014315:Triterpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001426:Bacterial Proteins; D014315:Triterpenes; C025206:hopane; D000637:Transaminases; D009699:N-Glycosyl Hydrolases
keywords: Streptomyces coelicolor; biosynthesis; hopanoids; ribosylhopane; terpenoids