Directed Biosynthesis of Unnatural Ergot Peptide Alkaloids

Journal of Natural Products
1992.0

Abstract

Three unnatural lysergic derivatives belonging to the class of ergopeptines have been obtained by feeding L-norvaline to a strain of Clayircppwpm. Ergorine (11 corresponds to an analogue of ergovaline, and ergonorine 121 is an analogue of ergocornine; both have at C-5' an n-propyl substituent instead of an isopropyl group. Ergonornorine (31 has the npropyl group at C-2' and C-5' as well. This alkaloid represents the first example ofan ergopeptine having an unnatural amino acid in the first position ofthe cyclol moiety. Additional feeding experiments with natural and unnatural amino acids indicated the maximum possible size of the substitutent in the first position of the peptide moiety.

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