Biosynthesis of diisocyanoadociane, a novel diterpene from the marine sponge Amphimedon sp. Crystal structure of a monoamide derivative

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Abstract
Sodium [14C] cyanide is efficiently incorporated into diisocyanoadociane [1,8-di-isocyano-1,2,5,8-tetramethylperhydropyrene, (1)], 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. Zinc [14C] cyanide and isobutyraldehyde [14C] cyanohydrin are effective precursor alternatives to sodium [14C] 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 [U-14C] alanine, [2-14C]glycine, [U-14C]leucine and [guanidine-14C]arginine; none of these precursors were used for isocyanide synthesis. Single X-ray crystallographic structure analysis of a p-bromobenzamide degradation product (17) established that the absolute configuration for diisocyanoadociane is (1R,2R,3aS,5S,6R,8S,8aS,10aS,10bS,10cS).

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