Biosynthesis of the Trehalase Inhibitor Trehazolin

Access this Article

Search this Article

Author(s)

    • SUGIYAMA Yasumasa
    • Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo
    • NAGASAWA Hiromichi
    • Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo
    • SUZUKI Akinori
    • Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo
    • SAKUDA Shohei
    • Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo

Abstract

Trehazolin (<b>1</b>) is a trehalase inhibitor produced by <i>Micromonospora coriacea</i>. Biosynthesis of <b>1</b> was studied by feeding experiments with a variety of labeled precursors. Feeding experiments with [1-<sup>13</sup>C]- and [6-<sup>13</sup>C]-D-glucose revealed that the carbon skeletons of both a glucose residue and a cyclopentane ring moiety in <b>1</b> 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-<sup>13</sup>C, <sup>15</sup>N<sub>2</sub>]-L-arginine revealed that two nitrogen atoms and a quaternary carbon atom involved in the aminooxazoline moiety of <b>1</b> originated from an amidino group of arginine. Further feeding experiments with [1-<sup>2</sup>H]-, [2-<sup>2</sup>H]-, [4-<sup>2</sup>H]-, [6, 6-<sup>2</sup>H<sub>2</sub>]- and [1, 2, 3, 4, 5, 6, 6-<sup>2</sup>H<sub>7</sub>]-D-glucose as well as [1-<sup>13</sup>C]-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 <b>1</b>.

Journal

  • The Journal of Antibiotics

    The Journal of Antibiotics 55(3), 263-269, 2002-03-25

    JAPAN ANTIBIOTICS RESEARCH ASSOCIATION

References:  19

Codes

Page Top