Insight into C35 terpene Biosyntheses by Nonpathogenic Mycobacterium Species: Functional Analyses of Three Z-Prenyltransferases and Identification of Dehydroheptaprenylcyclines
✍ Scribed by Tsutomu Sato; Kazuo Takizawa; Yuriko Orito; Hanayo Kudo; Tsutomu Hoshino
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 344 KB
- Volume
- 11
- Category
- Article
- ISSN
- 1439-4227
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✦ Synopsis
Nonpathogenic Mycobacterium species produce rare cyclic C(35) terpenes that are biosynthesized by cyclization of Z-type C(35) polyprenyl diphosphate. To provide deeper insight into the biosynthesis of C(35) terpenes, we carried out functional analyses of three Z-prenyltransferase homologues in M. vanbaalenii identified by genomic analysis. Mvan_3822, a novel bifunctional Z-prenyltransferase, biosynthesizes C(35)-heptaprenyl diphosphate as a main product from (E,E)-farnesyl diphosphate (E,E-FPP) and (E,E,E)-geranylgeranyl diphosphate (E,E,E-GGPP), but produces a C(50)-decaprenyl diphosphate from geranyl diphosphate. Mvan_1705 is a novel Z,E,E-GGPP synthase. In addition, novel cyclic C(35) terpenes, (14E)- and (14Z)-dehydroheptaprenylcycline, were identified as minor metabolites in nonpathogenic Mycobacterium cells. C(35) terpenes could be biosynthesized by two routes, in which E and Z geometric isomers of heptaprenyl diphosphate are produced from E,E-FPP and E,E,E-GGPP, and the prenylreductase responsible for the biosynthesis of C(35) terpenes could reduce both E and Z prenyl residues.