Biosynthetic studies on the chitinase inhibitor, allosamidin. Origin of the carbon and nitrogen atoms

Abstract

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 [1-¹³C]- and D-[6-¹³C]glucose as well as doubly labelled D-[1-¹³C,2-¹⁵N]-glucosamine revealed that each skeleton of N-acetyl-D-allosamine and allosamizoline 2 was derived from D-glucosamine. Further experiments with L-[guanidino-¹³C,¹⁵N₂]arginine and [methyl-^l3C]-methionine clarified the origin of the dimethylaminooxazoline moiety of compound 2.