132729-37-4Relevant articles and documents
Biosynthesis of the trehalase inhibitor trehazolin
Sugiyama, Yasumasa,Nagasawa, Hiromichi,Suzuki, Akinori,Sakuda, Shohei
, p. 263 - 269 (2002)
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.
Total synthesis of (+)-trehazolin: Optically active spirocycloheptadienes as useful precursors for the synthesis of aminocyclopentitols
Ledford, Brian E.,Carreira, Erick M.
, p. 11811 - 11812 (2007/10/03)
-
Total Synthesis of the Trehalase Inhibitors Trehalostatin and Trehazolin, and of Their Diastereoisomers. Final Structural Confirmation of the Inhibitor
Uchida, Chikara,Yamagishi, Tatsuya,Ogawa, Seiichiro
, p. 589 - 602 (2007/10/02)
Potent trehalase inhibitors 1-4 have been synthesized, thereby establishing both the structure and the absolute configuration of the known inhibitor trehazolin 2.Compound 1, previously proposed as the structure of trehalostatin, and its diastereoisomer 3,
