Synthesis of mannostatins A and B from myo-inositol.
Mannostatins A and B, along with the respective enantiomer and diastereoisomer having the (S)-sulfinyl function, were synthesized from myo-inositol. Inhibitory activity of the synthetic compounds against jack bean alpha-mannosidase was measured, revealing that the 4-aminocyclopentane-1,2,3-triol structure plays a major role in interaction with the enzyme.
Ogawa
S
S
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Yu
Y
Y
D003517:Cyclopentanes / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007887:Fabaceae / Q000201:enzymology; D007294:Inositol / Q000737:chemistry*; D008361:Mannosidases / Q000037:antagonists & inhibitors*; D010946:Plants, Medicinal; D013329:Structure-Activity Relationship; D043323:alpha-Mannosidase
D003517:Cyclopentanes; D004791:Enzyme Inhibitors; C060107:mannostatin A; C060108:mannostatin B; D007294:Inositol; D008361:Mannosidases; D043323:alpha-Mannosidase