Trichodiene synthase: Mechanism-based inhibition of a sesquiterpene cyclase
The farnesyl diphosphate analog 5 was shown to be a mechanism-based inhibitor of trichodiene synthase. Evidence of anamolous turnover products from extracts of incubation mixtures indicates 5 also serves as substrate of the enzyme.
References (26)
- et al.
Gene
(1989)et al.Arch. Biochem. Biophys.
(1989) - et al.
Arch. Biochem. Biophys.
(1993) - et al.
Bioorg. Chem.
(1985)et al.J. Am. Chem. Soc.
(1988) - et al.
Biochemistry
(1995) - et al.
Biochemistry
(1990) Pure Appl. Chem.
(1964)et al.Chem. Rev.
(1989)- et al.
J. Org. Chem.
(1986) Encyclopedia of Terpenoids
(1982)Chem. Rev.
(1990)Acc. Chem. Res.
(1985)
Science
Science
J. Chem. Soc., Perkin Trans. 1
Cited by (14)
Carbon sources as factors affecting the secondary metabolism of the maize pathogen Fusarium verticillioides
2019, LWTCitation Excerpt :According to our results, carbon sources have a strong effect on sesquiterpene emissions. It is well known that different sesquiterpene synthases are responsible for the formation of different sesquiterpenes or group of sesquiterpenes from a single common precursor, farnesyl diphosphate (Cane & Bowser, 1999). Besides, some sesquiterpenes are precursors in the biosynthesis of others, for example, germacrene is the intermediate precursor of β-elemene, both detected in our experiments (Brock, Tudzynski, & Dickschat, 2011).
Structure of a three-domain sesquiterpene synthase: A prospective target for advanced biofuels production
2011, StructureCitation Excerpt :Therefore, in TS there is no stabilization of the bisabolyl carbocation and subsequent removal of a hydrogen atom at C9. Instead, the proximity of the empty p orbital of C7 and the C10-C11 π orbital, result in C7-C11 bond formation and a second carbocation intermediate (Cane and Bowser, 1999), which ultimately leads to the formation of trichodiene. The presence of both a γ domain and a pocket in the β-γ interface for a potential terpene synthase Class II active site makes AgBIS the structurally characterized sesquiterpene synthase most closely related to diterpene synthases.
Navigating Past a Fork in the Road: Carbocation-π Interactions Can Manipulate Dynamic Behavior of Reactions Facing Post-Transition-State Bifurcations
2017, Journal of the American Chemical SocietyA tangled web-interconnecting pathways to amorphadiene and the amorphene sesquiterpenes
2010, Chemical Science