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Ribosylhopane, a Novel Bacterial Hopanoid, as Precursor of C35 Bacteriohopanepolyols in Streptomyces coelicolor A3(2)

Lookup NU author(s): Dr Helen Talbot


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Wild-type Streptomyces coelicolor A3(2) produces aminobacteriohopanetriol as the only elongated C-35 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 C-35 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.

Publication metadata

Author(s): Liu WJ, Sakr E, Schaeffer P, Talbot HM, Donisi J, Hartner T, Kannenberg E, Takano E, Rohmer M

Publication type: Article

Publication status: Published

Journal: ChemBioChem

Year: 2014

Volume: 15

Issue: 14

Pages: 2156-2161

Print publication date: 22/09/2014

Online publication date: 22/08/2014

ISSN (print): 1439-4227

ISSN (electronic): 1439-7633

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA


DOI: 10.1002/cbic.201402261


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Funder referenceFunder name
French embassy in Beijing
Alexander von Humboldt Foundation
China Scholarship Council
Foundation Frontier Research in Chemistry (Strasbourg, France)
Science Research Investment Fund (SRIF) from HEFCE
University of Tubingen
DE-FG02-09ER20097United States Department of Energy
SFB 766Deutsche Forschungsgemeinschaft
R21 AI76753United States National Institutes of Health