85-1487-76　Deoxyfuconojirimycin Hydrochloride (DFJ) 10mg　CAS No:210174-73-5　D3187-83D

特徴

• A powerful and specific inhibitor of several alpha-L-fucosidases. Deoxyfuconojirimycin (1,5-dideoxy-1,5-imino-L-fucitol) is a potent, specific and competitive inhibitor (Ki 1 x 10(-8) M) of human liver alpha-L-fucosidase (EC 3.2.1.51). Six structural analogues of this compound were synthesized and tested for their ability to inhibit alpha-L-fucosidase and other human liver glycosidases. It is concluded that the minimum structural requirement for inhibition of alpha-L-fucosidase is the correct configuration of the hydroxy groups at the piperidine ring carbon atoms 2, 3 and 4. Different substituents in either configuration at carbon atom 1 (i.e. 1 alpha- and beta-homofuconojirimycins) and at carbon atom 5 may alter the potency but do not destroy the inhibition of alpha-L-fucosidase. The pH-dependency of the inhibition by these amino sugars suggests very strongly that inhibition results from the formation of an ion-pair between the protonated inhibitor and a carboxylate group in the active site of the enzyme. Deoxymannojirimycin (1,5-dideoxy-1,5-imino-D-mannitol) is also a more potent inhibitor of alpha-L-fucosidase than of alpha-D-mannosidase. This can be explained by viewing deoxymannojirimycin as beta-L-homofuconojirimycin lacking the 5-methyl group. Conversely, beta-L-homo analogues of fuconojirimycin can also be regarded as derivatives of deoxymannojirimycin. This has permitted deductions to be made about the structural requirements of inhibitors of alpha- and beta-D-mannosidases.
• Synonyms:(2S,3R,4S,5R)-2-Methyl-3,4,5-piperidinetriol; 1,5-Dideoxy-1,5-imino-L-fucitol
• Molecular Formula:C6H13NO3•HCl
• Molecular Weight:183.63
• Appearance:Beige solid
• Purity:~98%
• Method for Detemining Identity:Proton NMR (D2O) and MS
• Melting Point:186-188°C
• TLC Conditions:C18; Methanol: Water (20 : 1). Visualized with UV and AMCS (single spot; Rf =0.7)
• Microanalysis (%):Calculated:C: 35.74, H:8.00, N: 6.95, Cl:17.58
• Storage and Stability:Store under inert atmosphere at 4°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.