Parent Class:

EC-Numbers → 1 -- Oxidoreductases → 1.14 -- Acting on paired donors, with incorporation or reduction of molecular oxygen → 1.14.20 -- With 2-oxoglutarate as one donor, and the other dehydrogenated

Synonyms: isnB (gene name)

Systematic Name: (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate,2-oxoglutarate:oxygen oxidoreductase (decarboxylating, 3-[(E)-2-isocyanoethenyl]-1H-indole-forming)

Unification Links: BRENDA:1.14.20.12, ENZYME:1.14.20.12, IUBMB-ExplorEnz:1.14.20.12

Reaction:
(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + 2-oxoglutarate + dioxygen + H⁺ → 3-[(E)-2-isocyanoethenyl]-1H-indole + succinate + 2 CO₂ + H₂O

Enzymes and Genes:
L-tryptophan isonitrile desaturase/decarboxylase (3-[(E)-2-isocyanoethenyl]-1H-indole-forming): isnB ( bacterium )

Summary:
The enzyme has been characterized from an unidentified soil bacterium. It catalyzes an Fe²⁺, 2-oxoglutarate-dependent monooxygenation at C-3, which is followed by decarboxylation and dehydration, resulting in the generation of a trans C-C double bond. cf EC 1.14.20.11, 3-[(Z)-2-isocyanoethenyl]-1H-indole synthase.

Citations: [Brady05, Chang17]

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References

Brady05: Brady SF, Clardy J (2005). "Cloning and heterologous expression of isocyanide biosynthetic genes from environmental DNA." Angew Chem Int Ed Engl 44(43);7063-5. PMID: 16206308

Chang17: Chang WC, Sanyal D, Huang JL, Ittiamornkul K, Zhu Q, Liu X (2017). "In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate." Org Lett 19(5);1208-1211. PMID: 28212039

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Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 46(D1):D633-D639 2018
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