RRC ID 15668
Author Sato T, Kigawa A, Takagi R, Adachi T, Hoshino T.
Title Biosynthesis of a novel cyclic C35-terpene via the cyclisation of a Z-type C35-polyprenyl diphosphate obtained from a nonpathogenic Mycobacterium species.
Journal Org Biomol Chem
Abstract Lipid components from 12 nonpathogenic Mycobacterium species were analysed. A novel cyclic C(35)-terpene, named heptaprenylcycline , was obtained from 3 species, while octahydroheptaprenol , which has 3 Z-double bonds, was obtained from 6 species. The amounts of and in the cultured cells increased after the 4- to 6-d stationary phase. The yield of was considerably greater at a higher temperature of 37 degrees C than at an optimal temperature of 28 degrees C, while that of remained unchanged at all temperatures. A feeding experiment with d-[1-(13)C]glucose revealed that was produced via isopentenyl diphosphate, which is a metabolite of glycolysis and the methylerythritol phosphate pathway. The conversion of octahydroheptaprenyl diphosphate to was successful by using the cell-free extracts of M. chlorophenolicum, demonstrating that is the biosynthetic intermediate of . This is the first example of the biosynthesis of a natural terpene via the cyclisation of a linear C(35)-isoprenoid. The substrate for C(35)-terpene cyclase has Z-type prenyl moieties; however, terpene cyclases usually employ E-type isoprenoids. The gene encoding the terpene cyclase that cyclises prenyl diphosphate containing Z-double bonds as the natural substrate has not yet been detected. Despite a careful search using the FASTA3 program, we could not detect any gene that is homologous to the known diphosphate-triggered type of mono-, sesqui- and diterpene cyclases in the genome of M. vanbaalenii, the DNA sequence of which has recently been elucidated. This suggests that a novel type of terpene cyclase might exist in the nonpathogenic Mycobacterium species.
Volume 6(20)
Pages 3788-94
Published 2008-10-21
DOI 10.1039/b808513g
PMID 18843409
MeSH Culture Media Cyclization Diphosphates / chemistry* Diphosphates / metabolism* Lipids / analysis Mycobacterium / chemistry* Mycobacterium / metabolism* Triterpenes / analysis* Triterpenes / isolation & purification Triterpenes / metabolism*
IF 3.412
Times Cited 19
General Microbes JCM 6362 JCM 6364 JCM 6366 JCM 6367 JCM 6370 JCM 6371 JCM 6375 JCM 6376 JCM 6377 JCM 6386 JCM 7439 JCM 13017