Studies on synthesis of 3-O-alkyl-D-glucose and 3-O-alkyl-D-allose derivatives and their biological activities.

Abstract

Studieson Synthesis of 3-ƒ--Alkyl-D-glucose and 3-ƒ--Alkyl-Dallose Derivatives and Their Biological Activities TETSURO IKEKAWA,*, a KAZUHIKO IRINODA,a, 1 ) KOICHI SAZE,a TATSUHIKO KATORI ,b

Second‐Generation Iminoxylitol‐Based Pharmacological Chaperones for the Treatment of Gaucher Disease

“…The expeditious synthesis of 3-O-hexyl-DIX 16 was performed in five steps with minimal protecting group manipulations, by following the same synthetic strategy (Scheme 2). Direct 3-O-alkylation of diacetone-d-glucose 5 [29] followed by regioselective hydrolysis of the less stable isopropylidene acetal and sodium periodate mediated diol cleavage afforded aldehyde 14.…”

An expression system to screen for inhibitors of parasite glucose transporters

“…3- O -Undec-10-enyl- d -glucose (compound 3361) was synthesized as described [19]. 1,2:5,6-Di- O -isopropylidene-α- d -glucofuranose (2.6 g) was dissolved in 15ml anhydrous DMSO and treated with 15 ml of 1.4M solution of NaH in anhydrous DMSO (15ml) dropwise while the solution was stirred and maintained at room temperature, followed by the dropwise addition of 11-bromo-1-undecene (4.29 g).…”

Anti-proliferative activity of 6-O-acyl-d-allose against the human leukemia MOLT-4F cell line

“…Since it has previously been reported that Dglucose had little effect on the proliferation of MOLT-4F cells, even at 20 mM, 4) these results indicate that the D-allose moiety was important for this inhibitory activity. GI 50 values, the concentration required to inhibit cell growth by 50%, estimated from dose-response curves are listed in 14) However, the inhibitory effects of D-allose ethers were about 5-100-fold weaker than those of the corresponding D-glucose ethers. Therefore, modifying at the C-6 position of D-allose may be promising for the development of stronger anti-proliferative compounds that retain the unique activity of this rare sugar.…”