2,5-dideoxy-2,5-imino-d-mannitol and -d-glucitol. Two-step bio-organic syntheses from 5-azido-5-deoxy-d-glucofuranose and -l-idofuranose; evaluation as glucosidase inhibitors and application in affinity purification and characterisation of invertase from yeast
✍ Scribed by Günter Legler; Annette Korth; Andreas Berger; Christian Ekhart; Günther Gradnig; Arnold E. Stütz
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- English
- Weight
- 847 KB
- Volume
- 250
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Glucose isomerase (EC 5.3.1.5) catalyzes the quantitative isomerisation of 5-azido-5-deoxy-n-gluco-(7) and -L-idofuranose (9), respectively, into the corresponding ketoses, 5-azido-5-deoxy-n-fructopyranose (8) and -L-sorbopyranose (lo), respectively. Upon catalytic hydrogenation over palladium-oncharcoal, the fructose derivative 8 gives the natural product and the efficient glycosidase inhibitor 2,5-dideoxy-2,5-imino-n-mannitol (41, while the sorbose derivative 10 affords 2,5-dideoxy-2,5-imino-Dglucitol (5). This represents a preparatively very simple and efficient two-step synthesis of these biologically active compounds. Both are strong inhibitors of a-and fi-glucosidases from various sources, the D-manno-isomer 4 being distinctly more active. Because of its structural relationship with p-D-fructofuranose, compound 4 is also a very good inhibitor of invertase from yeast and, as such, was for the first time employed, after immobilization on aminohexyl-sepharose, for the purification of this enzyme.