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pre-sodorifen diphosphate
sodorifen + diphosphate
additional information
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pre-sodorifen diphosphate
sodorifen + diphosphate
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Substrates: -
Products: -
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pre-sodorifen diphosphate
sodorifen + diphosphate
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Substrates: -
Products: -
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pre-sodorifen diphosphate
sodorifen + diphosphate
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Substrates: -
Products: -
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additional information
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A0A1B1KQP0
Substrates: enzyme is a multi-product terpene synthase that produces a set of sodorifen like terpenes simultaneously
Products: -
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additional information
?
-
A0A1B1KQP0
Substrates: enzyme is a multi-product terpene synthase that produces a set of sodorifen like terpenes simultaneously
Products: -
?
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metabolism
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reaction starts with the ionization of presodorifen diphosphate by abstraction of diphosphate to the presodorifenyl cation, which can undergo a 1,4-proton shift of the 4-pro-S hydrogen. The same hydrogen is then transferred through a 1,2-hydride shift to C-10 and after fragmentation into a pentadienyl cation and a cyclopentene portion to C-1, explaining its observed net migration from C-4 to C-1. Rotation of the pentadiene fragment brings C-5 into proximity of H-7, which allows for a proton transfer. After further rotation, the two fragments are recombined in a [4 + 3] cycloaddition with attack of C-10 to C-4 and attack of C-2 to C-7, either concertedly or stepwise. Wagner-Meerwein rearrangement and deprotonation lead to sodorifen
physiological function
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the sodorifen gene cluster consists of genes SOD c20750, SOD c20760, SOD c20770 and SOD c20780, encoding a terpene cyclase, methyltransferase, deoxy-xylulose-5-phosphate synthase and isopentenyl pyrophosphate isomerase, respectively. Gene product of SOD c20770 is dispensable for sodorifen synthesis
physiological function
A0A1B1KQP0
upon coexpression of the synthase and methyltransferase genes Q5A_011535 and Q5A_011540 in an Escherichia coli strain overproducing farnesyl diphosphate, formation of sodorifen is detected in the headspace of Escherichia coli cultures
physiological function
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Serratia plymuthica C-methyltransferase and sodorifen terpene cyclase act sequentially to convert farnesyl phosphate into sodorifen via a pre-sodorifen diphosphate intermediate
physiological function
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upon coexpression of the synthase and methyltransferase genes Q5A_011535 and Q5A_011540 in an Escherichia coli strain overproducing farnesyl diphosphate, formation of sodorifen is detected in the headspace of Escherichia coli cultures
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physiological function
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the sodorifen gene cluster consists of genes SOD c20750, SOD c20760, SOD c20770 and SOD c20780, encoding a terpene cyclase, methyltransferase, deoxy-xylulose-5-phosphate synthase and isopentenyl pyrophosphate isomerase, respectively. Gene product of SOD c20770 is dispensable for sodorifen synthesis
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physiological function
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Serratia plymuthica C-methyltransferase and sodorifen terpene cyclase act sequentially to convert farnesyl phosphate into sodorifen via a pre-sodorifen diphosphate intermediate
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Domik, D.; Magnus, N.; Piechulla, B.
Analysis of a new cluster of genes involved in the synthesis of the unique volatile organic compound sodorifen of Serratia plymuthica 4Rx13
FEMS Microbiol. Lett.
363
fnw139
2016
Serratia plymuthica, Serratia plymuthica 4Rx13
brenda
Von Reuss, S.; Domik, D.; Lemfack, M.; Magnus, N.; Kai, M.; Weise, T.; Piechulla, B.
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
2018
Serratia plymuthica, Serratia plymuthica 4Rx13
brenda
Duell, E.; DAgostino, P.; Shapiro, N.; Woyke, T.; Fuchs, T.; Gulder, T.
Direct pathway cloning of the sodorifen biosynthetic gene cluster and recombinant generation of its product in E. coli
Microb. Cell Fact.
18
32
2019
Serratia plymuthica, Serratia plymuthica WS3236
brenda
Schmidt, R.; De Jager, V.; Zuehlke, D.; Wolff, C.; Bernhardt, J.; Cankar, K.; Beekwilder, J.; Van Ijcken, W.; Sleutels, F.; De Boer, W.; Riedel, K.; Garbeva, P.
Fungal volatile compounds induce production of the secondary metabolite sodorifen in Serratia plymuthica PRI-2C
Sci. Rep.
7
862
2017
Serratia plymuthica (A0A1B1KQP0), Serratia plymuthica PRI-2C (A0A1B1KQP0)
brenda
Xu, H.; Lauterbach, L.; Goldfuss, B.; Schnakenburg, G.; Dickschat, J.S.
Fragmentation and [4 + 3] cycloaddition in sodorifen biosynthesis
Nat. Chem.
15
1164-1171
2023
Serratia plymuthica
brenda
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