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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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Abstract

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

URL: http://dx.doi.org/10.1002/cbic.201402261

DOI: 10.1002/cbic.201402261

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