Modified Nucleosides || Clitocine and Its Analogues

✍ Scribed by Herdewijn, Piet

• Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
• Year: 2008
• Tongue: German
• Weight: 194 KB
• Edition: 1
• Category: Article
• ISBN: 3527318208
• DOI: 10.1002/9783527623112.ch22

✦ Synopsis

Guided by the insecticidal activity against the agricultural pest insect Pectinophora gossypiella, Kubo and Kim isolated clitocine (1a) [1], along with adenosine, from Clitocybe inversa, a medium-sized, buff-colored mushroom found in western North America. The NMR spectral data for clitocine was found to be very similar to that of adenosine, with the exception of the absence of the C-8 carbon peak of adenosine, while the low chemical shift of the 4-NH proton suggested strong hydrogen bonding between the 5-NO 2 and 4-NH groups. Later, Moss and coworkers [2] confirmed its structure through X-ray crystallographic analysis: as postulated earlier by Kubo et al., the entire aglycone moiety resembles a tricyclic ring system as a result of the hydrogen bonding between the 4-NH and 6-NH protons and the NO 2 group.