Abseits der Regel — Terpene mit ungewöhnlichen Kohlenstoffgerüsten
Tóm tắt
The natural substance class of terpenoids covers an extremely wide range of different structures, although their building block repertoire is strongly limited. Methyltransferases from bacterial natural product pathways can add carbon atoms to cellular terpene precursors and thereby expand the accessible chemical space of the products. Here we present examples for the application of such enzymes to produce novel and unusual terpene molecules.
Tài liệu tham khảo
Wallach O (1885) Zur Kenntnis der Terpene und ätherischen Öle. Liebigs Annalen 227: 277
Ruzicka L (1953) The isoprene rule and the biogenesis of terpenic compounds. Experientia 9: 357–367
Dickschat JS, Nawrath T, Thiel V et al. (2007) Biosynthesis of the off-flavor 2-methylisoborneol by the myxobacterium Nannocystis exedens. Angew Chem Int Ed Engl 46: 8287–8290
Komatsu M, Tsuda M, Omura S et al. (2008) Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol. Proc Natl Acad Sci U S A 105: 7422–7427
Wang CM, Cane DE (2008) Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor. J Am Chem Soc 130: 8908–8909
Kschowak MJ, Wortmann H, Dickschat JS et al. (2018) Heterologous expression of 2-methylisoborneol/2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes. PLoS One 13: e0196082
Kschowak MJ, Maier F, Wortmann H et al. (2020) Analyzing and engineering the product selectivity of a 2-methylenebornane synthase. ACS Synth Biol 9: 981–986
von Reuss S, Domik D, Lemfack MC et al. (2018) Sodorifen biosynthesis in the rhizobacterium Serratia plymuthica involves methylation and cyclization of MEP-derived farnesyl pyrophosphate by a SAM-dependent C-methyltransferase. J Am Chem Soc 140: 11855–11862
Drummond L, Kschowak MJ, Breitenbach J et al. (2019) Expanding the isoprenoid building block repertoire with an IPP methyltransferase from Streptomyces monomycini. ACS Synth Biol 8: 1303–1313
Ozaki T, Shinde SS, Gao L et al. (2018) Enzymatic formation of a skipped methyl-substituted octaprenyl side chain of longestin (KS-505a): involvement of homo-IPP as a common extender unit. Angew Chem Int Ed Engl 57: 6629–6632
Radhika V, Ueda N, Tsuboi Y et al. (2015) Methylated cytokinins from the phytopathogen Rhodococcus fascians mimic plant hormone activity. Plant Physiol 169: 1118–1126