Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100191, China.
Org Biomol Chem. 2011 May 7;9(9):3405-14. doi: 10.1039/c0ob01063d. Epub 2011 Mar 18.
L-DMDP and L-homoDMDP, the enantiomers of naturally occurring DMDP and homoDMDP have been synthesized from D-xylose derived cyclic nitrone 9. Their 3-deoxy-3-fluorinated analogues were also obtained from polyhydroxylated fluorinated cyclic nitrone 10, which was prepared from fluorinated sugar 12 in seven steps. Bioactivities of these iminosugars against various glycosidases were evaluated. While L-DMDP and L-homoDMDP are potent inhibitors of α-glucosidases, a sharp decrease of inhibition was found when the C-3 hydroxyl group of these compounds was replaced by fluoride, which showed the great importance of the C-3 hydroxyl in their interaction with enzymes.
L-DMDP 和 L-homoDMDP 是天然存在的 DMDP 和 homoDMDP 的对映异构体，已从 D-木糖衍生的环状硝酮 9 合成得到。它们的 3-脱氧-3-氟代类似物也从多羟基氟代环状硝酮 10 获得，10 是从氟代糖 12 经七步反应制备的。这些异头物对各种糖苷酶的生物活性进行了评价。虽然 L-DMDP 和 L-homoDMDP 是α-葡萄糖苷酶的有效抑制剂，但当这些化合物的 C-3 羟基被氟取代时，抑制作用急剧下降，这表明 C-3 羟基在它们与酶的相互作用中非常重要。
