Sirodesmin PL biosynthesis in Phoma lingam tode

Abstract

The biosynthesis of sirodesmin PL (1) in the fungus Phoma lingam Tode has been investigated using different labelled precursors : [1-14C]-, [1-13C]-, [1,2-13C2]-acetates, L-[U-14C]serine, L-[U-14C]tyrosine, [14C] phomamide (3) or [14C]cyclo-L-tyrosyl-L-serine (4). A scheme is proposed in agreement with the demonstration of the mevalonic origin of the tetrahydrofuranone ring, the incorporation of radioactivity from serine and tyrosine, and the easy conversion of the two cyclodipeptides (3) and (4) into sirodesmin PL (1).