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IUBMB CommentsThe enzyme is highly specific for alpha-D-sedoheptulopyranose 7-phosphate. It requires a divalent metal ion (Zn2+ or Co2+) and an NAD+ cofactor, which is transiently reduced during the reaction. The enzyme is involved in the biosynthesis of C7N-aminocyclitol natural products, such as the valienamine moiety of the antidiabetic drug acarbose and the crop protectant validamycin A. cf. EC 4.2.3.155, 2-epi-valiolone synthase and EC 4.2.3.154, demethyl-4-deoxygadusol synthase.
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D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
additional information
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D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
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D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the product 2-epi-5-epi-valiolone is a precursor in the biosynthesis of the cetoniacytones
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D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the product 2-epi-5-epi-valiolone is a precursor in the biosynthesis of the cetoniacytones
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the cyclization product, 2-epi-5-epi-valiolone is a precursor of the valienamine moiety of acarbose
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
no activity with ido-heptulose 7-phosphate
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the cyclization product, 2-epi-5-epi-valiolone is a precursor of the valienamine moiety of acarbose
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
no activity with ido-heptulose 7-phosphate
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the enzyme is involved in biosynthesis of 2-epi-5-epi-valiolone a precursor in the biosynthesis of C7N-aminocyclitol-containing natural products, such as validamycin and acarbose
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?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
SalQ has high specificity for sedoheptulose 7-phosphate as substrate. No activity with D-glucose 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate, 3-deoxy-D-arabino-heptulosonate 7-phosphate and D-ribose 5-phosphate
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?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the enzyme is involved in biosynthesis of 2-epi-5-epi-valiolone a precursor in the biosynthesis of C7N-aminocyclitol-containing natural products, such as validamycin and acarbose
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-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
SalQ has high specificity for sedoheptulose 7-phosphate as substrate. No activity with D-glucose 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate, 3-deoxy-D-arabino-heptulosonate 7-phosphate and D-ribose 5-phosphate
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D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
-
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
-
-
-
?
sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
-
-
-
?
sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
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-
-
?
additional information
?
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no substrates: amino 3-deoxy-D-arabino-heptulosonate 7-phosphate, 3-deoxy-D-arabino-heptulosonate 7-phosphate, glucose 6-phosphate, fructose 6-phosphate, mannose 6-phosphate, and ribose 5-phosphate
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?
additional information
?
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no substrates: amino 3-deoxy-D-arabino-heptulosonate 7-phosphate, 3-deoxy-D-arabino-heptulosonate 7-phosphate, glucose 6-phosphate, fructose 6-phosphate, mannose 6-phosphate, and ribose 5-phosphate
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?
additional information
?
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no substrates: amino 3-deoxy-D-arabino-heptulosonate 7-phosphate, 3-deoxy-D-arabino-heptulosonate 7-phosphate, glucose 6-phosphate, fructose 6-phosphate, mannose 6-phosphate, and ribose 5-phosphate
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?
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D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the product 2-epi-5-epi-valiolone is a precursor in the biosynthesis of the cetoniacytones
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the product 2-epi-5-epi-valiolone is a precursor in the biosynthesis of the cetoniacytones
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the cyclization product, 2-epi-5-epi-valiolone is a precursor of the valienamine moiety of acarbose
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the cyclization product, 2-epi-5-epi-valiolone is a precursor of the valienamine moiety of acarbose
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the enzyme is involved in biosynthesis of 2-epi-5-epi-valiolone a precursor in the biosynthesis of C7N-aminocyclitol-containing natural products, such as validamycin and acarbose
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
the enzyme is involved in biosynthesis of 2-epi-5-epi-valiolone a precursor in the biosynthesis of C7N-aminocyclitol-containing natural products, such as validamycin and acarbose
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
-
-
-
?
D-sedoheptulose 7-phosphate
2-epi-5-epi-valiolone + phosphate
-
-
-
?
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malfunction
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in-frame complete deletion of the 2-epi-5-epi-valiolone synthase gene has little effect on in vivo production of shinorine. Complete segregation of the 2-epi-5-epi-Valiolone synthase gene deletion mutant proves difficult and is achieved only when the mutant is grown in the dark and in a medium supplemented with fructose. The segregated mutant shows a striking colour change from native bluegreen to pale yellow-green, corresponding to substantial loss of the photosynthetic pigment phycocyanin, as evinced by combinations of absorbance and emission spectra. Transcriptional analysis of the mutant grown in the presence of fructose under dark or light conditions reveals downregulation of the cpcA gene that encodes the alpha subunit of phycocyanin, whereas the gene encoding nblA, a protease chaperone essential for phycobilisome degradation, is not expressed
metabolism
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2-epi-5-epi-valiolone synthase activity is essential for maintaining phycobilisome composition in the cyanobacterium Anabaena variabilis ATCC 29413 when grown in the presence of a carbon source
physiological function
the enzyme is involved in biosynthesis of 2-epi-5-epi-valiolone a precursor in the biosynthesis of C7N-aminocyclitol-containing natural products, such as validamycin and acarbose
physiological function
the product 2-epi-5-epi-valiolone is a precursor in the biosynthesis of the cetoniacytones
physiological function
-
the product 2-epi-5-epi-valiolone is a precursor in the biosynthesis of the cetoniacytones
-
physiological function
-
the enzyme is involved in biosynthesis of 2-epi-5-epi-valiolone a precursor in the biosynthesis of C7N-aminocyclitol-containing natural products, such as validamycin and acarbose
-
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Choi, W.S.; Wu, X.; Choeng, Y.H.; Mahmud, T.; Jeong, B.C.; Lee, S.H.; Chang, Y.K.; Kim, C.J.; Hong, S.K.
Genetic organization of the putative salbostatin biosynthetic gene cluster including the 2-epi-5-epi-valiolone synthase gene in Streptomyces albus ATCC 21838
Appl. Microbiol. Biotechnol.
80
637-645
2008
Streptomyces albus (A8D7K2), Streptomyces albus ATCC 21838 (A8D7K2), Streptomyces albus ATCC 21838
brenda
Kean, K.M.; Codding, S.J.; Asamizu, S.; Mahmud, T.; Karplus, P.A.
Structure of a sedoheptulose 7-phosphate cyclase: ValA from Streptomyces hygroscopicus
Biochemistry
53
4250-4260
2014
Streptomyces hygroscopicus (H2K887), Streptomyces hygroscopicus, Streptomyces hygroscopicus 5008 (H2K887)
brenda
Wu, X.; Flatt, P.M.; Schlrke, O.; Zeeck, A.; Dairi, T.; Mahmud, T.
A comparative analysis of the sugar phosphate cyclase superfamily involved in primary and secondary metabolism
Chembiochem
8(2)
239-248
2007
Actinomyces sp. (A1YPR2), Actinomyces sp., Actinomyces sp. Lu 9419 (A1YPR2)
brenda
Stratmann, A.; Mahmud, T.; Lee, S.; Distler, J.; Floss, H.G.; Piepersberg, W.
The AcbC protein from Actinoplanes species is a C7-cyclitol synthase related to 3-dehydroquinate synthases and is involved in the biosynthesis of the alpha-glucosidase inhibitor acarbose
J. Biol. Chem.
274
10889-10896
1999
Actinoplanes sp. (Q9ZAE9), Actinoplanes sp. 50/110 (Q9ZAE9)
brenda
Spence, E.; Bryan, S.J.; Lisfi, M.; Cullum, J.; Dunlap, W.C.; Shick, J.M.; Mullineaux, C.W.; Long, P.F.
2-epi-5-epi-Valiolone synthase activity is essential for maintaining phycobilisome composition in the cyanobacterium Anabaena variabilis ATCC 29413 when grown in the presence of a carbon source
Photosynth. Res.
116
33-43
2013
Trichormus variabilis
brenda