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Literature summary extracted from

  • Li, S.; Lowell, A.N.; Yu, F.; Raveh, A.; Newmister, S.A.; Bair, N.; Schaub, J.M.; Williams, R.M.; Sherman, D.H.
    Hapalindole/ambiguine biogenesis is mediated by a cope rearrangement, C-C bond-forming cascade (2015), J. Am. Chem. Soc., 137, 15366-15369 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.146 expressed in Escherichia coli BL21(DE3) cells Fischerella ambigua

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.146 3-[(E)-2-isocyanoethenyl]-1H-indole + geranyl diphosphate Fischerella ambigua preferred reaction 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole
-
 ?
2.5.1.146 3-[(E)-2-isocyanoethenyl]-1H-indole + geranyl diphosphate Fischerella ambigua UTEX 1903 preferred reaction 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.146 Fischerella ambigua
-
-
-
2.5.1.146 Fischerella ambigua UTEX 1903
-
-
-
5.5.1.32 Fischerella ambigua A0A076N4W8
-
-
5.5.1.32 Fischerella ambigua UTEX 19030 A0A076N4W8
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.146 3-[(E)-2-isocyanoethenyl]-1H-indole + dimethylallyl diphosphate
-
 Fischerella ambigua 3-[(E)-2-isocyanoethenyl]-2-(3-methylbut-2-en-1-yl)-1H-indole + 3-[(E)-2-isocyanoethenyl]-3-(3-methylbut-2-en-1-yl)-3H-indole
-
 ?
2.5.1.146 3-[(E)-2-isocyanoethenyl]-1H-indole + dimethylallyl diphosphate
-
 Fischerella ambigua UTEX 1903 3-[(E)-2-isocyanoethenyl]-2-(3-methylbut-2-en-1-yl)-1H-indole + 3-[(E)-2-isocyanoethenyl]-3-(3-methylbut-2-en-1-yl)-3H-indole
-
 ?
2.5.1.146 3-[(E)-2-isocyanoethenyl]-1H-indole + geranyl diphosphate preferred reaction Fischerella ambigua 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole
-
 ?
2.5.1.146 3-[(E)-2-isocyanoethenyl]-1H-indole + geranyl diphosphate preferred reaction Fischerella ambigua UTEX 1903 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole
-
 ?
5.5.1.32 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole
-
 Fischerella ambigua 12-epi-hapalindole U
-
 ?
5.5.1.32 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole
-
 Fischerella ambigua UTEX 19030 12-epi-hapalindole U
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.146 famD2
-
 Fischerella ambigua
5.5.1.32 famC1
-
 Fischerella ambigua

General Information

EC Number General Information Comment Organism
5.5.1.32 physiological function aromatic prenyltransferase FamD2 and FamC1 act in concert to form the tetracyclic core ring system of the hapalindoles from cis-indole isonitrile and geranyl diphosphate through a presumed biosynthetic Cope rearrangement and subsequent 6-exo-trig cyclization/electrophilic aromatic substitution reaction Fischerella ambigua