BIOSYNTHETIC-STUDIES ON THE CHITINASE INHIBITOR, ALLOSAMIDIN - ORIGIN OF THE CARBON AND NITROGEN-ATOMS

Allosamidin 1 is a potent insect chitinase inhibitor produced by Streptomyces sp. The biosynthesis of compound 1 was studied by feeding experiments with labelled precursors. Incorporation experiments using [1-C-13]- and D-[6-C-13]glucose as well as doubly labelled D-[1-C-13,2-N-15]-glucosamine revealed that each skeleton of N-acetyl-D-allosamine and allosamizoline 2 was derived froM D-glucosamine. Further experiments with L-[guanidino-C-13,N-15(2)]arginine and [methyl-C-13]-methionine clarified the origin of the dimethylaminooxazoline moiety of compound 2.