Bacterial sterol surrogates. Biosynthesis of the side-chain of bacteriohopanetetrol and of a carbocyclic pseudopentose from 13C-labelled glucose in Zymomonas mobilis

Abstract

Incorporation of ¹³C-labelled glucose into the triterpenoids of the hopane series of Zymomonas mobilis confirmed the following: (i) a D-ribose derivative is the precursor of the side-chain of bacteriohopanetetrol; (ii) the skeleton of a novel carbocyclic pentofuranose analogue derives from a hexose by formation of a carbon–carbon bond between C(1) and C(5); (iii) isoprenic units are not synthesized via direct incorporation of simple glucose catabolites into the isoprenoid biosynthesis.