Enzymatic synthesis of a novel trehalose derivative, 3,3'-diketotrehalose, and its potential application as the trehalase enzyme inhibitor.
We reported the preparation of a novel trehalose derivative based on enzymatic oxidation of trehalose by water-soluble glucose-3-dehydrogenase (G3DH) from marine bacterium Halomonas sp. alpha-15 cells. The product of G3DH enzymatic conversion was 3,3'-diketotrehalose (3,3'dkT), a novel trehalose derivative of which both third hydroxy groups of glucopyranosides were oxidized. 3,3'dkT was revealed to show an inhibitory effect toward pig-kidney and Bombyx mori trehalases. The IC(50) values of 3,3'dkT were 0.8 and 2.5 mM and K(i) values were 0.2 and 0.6 mM for pig-kidney and for B. mori trehalases, respectively. In addition, 3,3'dkT did not show any inhibitory effect on both maltase and mannosidase activities. Therefore, 3,3'dkT was a specific inhibitor of trehalases.
Sode
K
K
Department of Biotechnology, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei, 184-8588, Tokyo, Japan. sode@cc.tuat.ac.jp
Akaike
E
E
Sugiura
H
H
Tsugawa
W
W
D000818:Animals; D001667:Binding, Competitive; D012831:Bombyx / Q000201:enzymology; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D042843:Glucose 1-Dehydrogenase; D005948:Glucose Dehydrogenases / Q000737:chemistry*; D020632:Halomonas / Q000201:enzymology; D007700:Kinetics; D014198:Trehalase / Q000037:antagonists & inhibitors*; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C423542:3,3'-diketotrehalose; D004791:Enzyme Inhibitors; D014199:Trehalose; D005948:Glucose Dehydrogenases; D042843:Glucose 1-Dehydrogenase; D014198:Trehalase