120591-16-4Relevant academic research and scientific papers
Biosynthesis of Diisocyanoadociane, a Novel Diterpene from the Marine Sponge Amphimedon sp. Crystal Structure of a Monoamide Derivative
Fookes, Christopher J. R.,Garson, Mary J.,MacLeod, John K.,Skelton, Brian W.,White, Allan H.
, p. 1003 - 1012 (2007/10/02)
Sodium cyanide is efficiently incorporated into diisocyanoadociane , the major metabolite of the haplosclerid sponge Amphimedon sp.It is established by stepwise chemical degradation that the radiolabel is associated with the two isocyanide carbons.Zinccyanide and isobutyraldehydecyanohydrin are effective precursor alternatives to sodium cyanide and more suitable for use in stable isotope study.Attempts to demonstrate an amino acid origin of the cyanide utilised by Amphimedon sp. include tracer studies with alanine, glycine, arginine; none of these precursors were used for isocyanide synthesis.Single X-ray crystallographic structure analysis of p-bromobenzamide degradation product (17) established that the absolute configuration for diisocyanoadociane is (1R,2R,3aS,5S,6R,8S,8aS,10aS,10bS,10cS).
