Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

Wantae Kim, Tzu-Yu Chen, Lide Cha, Grace Zhou, Kristi Xing, Nicholas Koenig Canty, Yan Zhang () and Wei-chen Chang ()
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Wantae Kim: University of Texas
Tzu-Yu Chen: NC State University
Lide Cha: NC State University
Grace Zhou: University of Texas
Kristi Xing: University of Texas
Nicholas Koenig Canty: NC State University
Yan Zhang: University of Texas
Wei-chen Chang: NC State University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Two different types of desaturations are employed by iron- and 2-oxoglutarate-dependent (Fe/2OG) enzymes to construct vinyl isonitrile and isocyanoacrylate moieties found in isonitrile-containing natural products. A substrate-bound protein structure reveals a plausible strategy to affect desaturation and hints at substrate promiscuity of these enzymes. Analogs are synthesized and used as mechanistic probes to validate structural observations. Instead of proceeding through hydroxylated intermediate as previously proposed, a plausible carbocation species is utilized to trigger C=C bond installation. These Fe/2OG enzymes can also accommodate analogs with opposite chirality and different functional groups including isonitrile-(D)-tyrosine, N-formyl tyrosine, and phloretic acid, while maintaining the reaction selectivity.

Date: 2022
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DOI: 10.1038/s41467-022-32870-4

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