N-Cyclohexylisocyanide is an isonitrile. Generally a toxic class of compounds (Goda, 2001), isonitriles are unusual in that they contain a formally mono-coordinated carbon atom (similar to the carbon atom in carbon monoxide). Because the isocyano group can react with both electrophiles and nucleophiles attached to the same carbon atom, isonitriles have proven to be versatile reagents in organic synthesis (Domling, 2002).
Isonitriles are produced naturally by a variety of organisms, including bacteria, fungi, and marine sponges. They often have antibiotic properties; xanthocillin, a compound produced by Penicillium notatum which has a wide spectrum of antibiotic activity, is an isonitrile (Hagedorn and Tönjes, Pharmazie, 1957).
The metabolism of isonitriles is not well understood. Currently, only one enzyme involved in isonitrile metabolism, isonitrile hydratase, has been identified (Goda et al., 2001; Goda et al., 2002). The second step shown in this pathway, in which N-cyclohexylformamide is converted to cyclohexylamine, is postulated, based on similar amide hydrolases.
The following is a text-format cyclohexylisocyanide pathway map. An organism which can initiate the pathway is given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (4k) format.
N-Cyclohexylisocyanide Pseudomonas putida N19-2 | | isonitrile | hydratase | v N-Cyclohexylformamide | | N-cyclohexylformamide | amidohydrolase | v Cyclohexylamine | | | v to the Cyclohexylsulfamate Pathway
Page Author: Carla Essenberg
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