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Literature summary for 5.5.1.20 extracted from

  • Kim, H.J.; Ruszczycky, M.W.; Choi, S.H.; Liu, Y.N.; Liu, H.W.
    Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A (2011), Nature, 473, 109-112.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 5.5.1.20

Cloned(Commentary)

Cloned (Comment) Organism
gene spnF, overexpression of N-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3) Saccharopolyspora spinosa

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information SpnF specifically accelerates the ring formation reaction with an estimated 500fold rate enhancement. The cyclization event is modelled as the sum of a first order and a Michaelis-Menten process and fits Saccharopolyspora spinosa

Organism

Organism UniProt Comment Textmining
Saccharopolyspora spinosa
-
 gene spnF
-

Purification (Commentary)

Purification (Comment) Organism
recombinant N-terminally His6-tagged enzyme from Escherichia coli strain BL21(DE3) Saccharopolyspora spinosa

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(3E,5E,7E,10R,12E,14E,17R,18S,22S)-22-ethyl-10,18-dihydroxy-17-methyloxacyclodocosa-3,5,7,12,14-pentaene-2,16-dione via intermediate 6, the SpnF-catalysed endomode syn-addition of an alkenyl to a dienyl functionality seems consistent with a Diels-Alder reaction, but a stepwise [4+2] cycloaddition mechanism, for example, one involving a dipolar intermediate such as 7, cannot be ruled out Saccharopolyspora spinosa (2R,3aS,5aS,6E,10S,14S,15R,17E,18aS,18bR)-10-ethyl-2,14-dihydroxy-15-methyl-2,3,3a,5a,10,11,12,13,14,15,18a,18b-dodecahydro-1H-indeno[5,4-e]oxacyclopentadecine-8,16-dione
-
 ?
additional information mode of formation of the complex perhydro-as-indacene moiety in spinosyn A, overview. No activity with keto-intermediate 3 Saccharopolyspora spinosa ?
-
 ?

Synonyms

Synonyms Comment Organism
solanapyrone synthase
-
 Saccharopolyspora spinosa
SpnF
-
 Saccharopolyspora spinosa

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.23
-
 (3E,5E,7E,10R,12E,14E,17R,18S,22S)-22-ethyl-10,18-dihydroxy-17-methyloxacyclodocosa-3,5,7,12,14-pentaene-2,16-dione pH and temperature not specified in the publication Saccharopolyspora spinosa

General Information

General Information Comment Organism
metabolism the Diels-Alder reaction is the key transformation in the biosynthesis of many cyclohexene-containing secondary metabolites. Cyclase SpnF catalyses a transannular [4+2] cycloaddition to form the cyclohexene ring in spinosyn A, it catalyzes the cyclization step of macrolactone Saccharopolyspora spinosa
physiological function the enzyme is involved in biosynthesis of spinosyn A, a tetracyclic polyketide-derived insecticide from Saccharopolyspora spinosa Saccharopolyspora spinosa