Identification of Isonitrile‐Containing Natural Products in Complex Biological Matrices through Ligation with Chlorooximes

Autor: Rebecca J. B. Schäfer, Kayla Wilson, Maurice Biedermann, Bradley S. Moore, Simon Sieber, Helma Wennemers
Rok vydání: 2022
Předmět:
Zdroj: Chemistry-A European Journal, 29 (6)
ISSN: 1521-3765
0947-6539
Popis: Isonitrile-containing natural products have garnered attention for their manifold bioactivities but are difficult to detect and isolate due to the chemical lability of the isonitrile functional group. Here, we used the isonitrile-chlorooxime ligation (INC) in a reactivity-based screening (RBS) protocol for the detection and isolation of alkaloid and terpene isonitriles in the cyanobacterium Fischerella ambigua and a marine sponge of the order Bubarida, respectively. A trifunctional probe bearing a chlorooxime moiety, a UV active aromatic moiety, and a bromine label facilitated the chemoselective reaction with isonitriles, UV-Vis spectroscopic detection, and mass spectrometric analysis. The INC-based RBS allowed for the detection, isolation, and structural elucidation of isonitriles in microgram quantities.
Chemistry - A European Journal, 29 (6)
ISSN:0947-6539
ISSN:1521-3765
Databáze: OpenAIRE
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