Biosynthesis of the trehalase inhibitor trehazolin.
Trehazolin (1) is a trehalase inhibitor produced by Micromonospora coriacea. Biosynthesis of 1 was studied by feeding experiments with a variety of labeled precursors. Feeding experiments with [1-13C]- and [6-13C]-D-glucose revealed that the carbon skeletons of both a glucose residue and a cyclopentane ring moiety in 1 were each derived from glucose, and that C-C bond formation between C-1 and C-5 of glucose occurred during the cyclopentane ring formation. Furthermore, an experiment with [guanidino-13C, 15N2]-L-arginine revealed that two nitrogen atoms and a quaternary carbon atom involved in the aminooxazoline moiety of 1 originated from an amidino group of arginine. Further feeding experiments with [1-2H]-, [2-2H]-, [4-2H]-, [6,6-2H2]- and [1,2,3,4,5,6,6-2H7]-D-glucose as well as [1-13C]-D-fructose showed that deuteriums on C-1, C-3, C-4 and C-6 of glucose were retained during the formation of the cyclopentane ring moiety of 1.
Sugiyama
Yasumasa
Y
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Japan.
Nagasawa
Hiromichi
H
Suzuki
Akinori
A
Sakuda
Shohei
S
D003470:Culture Media; D004187:Disaccharides / Q000096:biosynthesis*; D004791:Enzyme Inhibitors / Q000378:metabolism*; D008847:Micromonospora / Q000254:growth & development / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D014198:Trehalase / Q000037:antagonists & inhibitors*
D003470:Culture Media; D004187:Disaccharides; D004791:Enzyme Inhibitors; C071816:trehazolin; D014198:Trehalase