Synthesis of (+)-3,7,8-trideoxy-3,7-imino-d-threo-l-galacto-octitol and its inhibition of β-glucosidases

✍ Scribed by Alain Baudat; Sylviane Picasso; Pierre Vogel

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 871 KB
• Volume: 281
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00348-7

✦ Synopsis

The readily available 2,3:6,7-di-O-isopropylidene-I)-gb 'cero-D-gulo-heptono-l,4-1actone [(-)-5] was converted in four synihetic steps into the n,~w io~inooctitol (+)-3.7.8-trideoxy-3.7-imin~-I)othreo-I.-gahr'to-octitol [(+)-I0]. Al:hough the pipelidine unit of (+)-10 has the ab,solule COlffi[zuralion of ~.D-gahr'toollexopyra2a)sides. this imir, oalditol does not inhibit five commercially avaihlble ~ogalactosidases. However. (+)-10 was tbund Io be a good con~pctitivc inhibilor o1' /3ob, hl¢o,,idase,,, l'rolu alluond (K, ;~ 15 #M)and li't,dl C~thhr'elh.. saccharoh'tirum (K i = 41 pM).