Literature summary for 4.2.3.61 extracted from

O'Maille, P.E.; Chappell, J.; Noel, J.P.
Biosynthetic potential of sesquiterpene synthase: alternative product of tobacco 5-epi-aristolochene synthase (2006), Arch. Biochem. Biophys., 448, 73-82.

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Organism

Organism	UniProt	Comment	Textmining
Nicotiana tabacum	-	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
(2E,6E)-farnesyl diphosphate	-	Nicotiana tabacum	(+)-5-epiaristolochene + diphosphate	about 79% of hydrocarbon product, plus about 6% of (-)-4-epi-eremophilene, 3.6% of (+)-germacrene A and 22 hydrocarbons contributing about 12% of TEAS sesquiterpene products. The pathway to the by-products starts with a 1,6 cyclization of the (Z,E)-farnesyl cation, followed by a 1,2 hydride shift leading to a syn-6,10 ring closure which generates an acoradilyl cation. Elimination of a proton from either C12 or C13 of the isopropylidene tail of the acoradilyl cation readily explains the formation of ?-acoradiene. Alternatively, a 2,11 ring closure followed by elimination of a proton at C2 is the likely pathway to (-)-alpha-cedrene. A 3,11 ring closure of the acoradilyl cation is the most common event, based on the relative abundance of isomerization products observed, and is followed by Wagner-Meerwein rearrangement and proton elimination from C15 to produce isoprezizaene, the dominant (Z,E)-farnesyl cation-derived product	?

Synonyms

Synonyms	Comment	Organism
TEAS	-	Nicotiana tabacum

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Release 2023.1 (January 2023)