Structure and synthesis of phomamide, a new piperazine-2,5-dione related to the sirodesmins, isolated from the culture medium of Phoma lingam Tode
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 113-115
- https://doi.org/10.1039/p19800000113
Abstract
Several active substances are produced by the fungus Phoma lingam Tode, among which are the previously reported sirodesmins PL (1) and (2), sulphur-containing piperazinediones. A new metabolite, phomamide, also a piperazine-2,5-dione, has now been isolated from the culture filtrate of the same fungus. On the basis of physicochemical and spectroscopical data, the structure (3) of cyclo-O-(γγ-dimethylallyl)-L-tyrosyl-L-serine has been demonstrated for this compound and confirmed through subsequent synthesis. This metabolite is assumed to be an intermediate in the biosynthesis of the sirodesmin group of antibiotics.Keywords
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