Synthesis of 1,4-dideoxy-1,4-imino-D-glucitol, a glucosidase inhibitor |
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| Authors: | J Kuszmann L Kiss |
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| Institution: | 1. School of Life Science, Anhui University, Hefei, Anhui Province, China;2. Anhui Key Laboratory of Modern Biomanufacturing, Anhui University, Hefei，Anhui Province, China;3. School of Chemistry and Chemical Engineering, Anhui University, Hefei, Anhui Province, China;1. Department of Psychiatry, University of Perugia, Perugia, Italy;2. Bipolar and Depressive Disorders Unit, Hospital Clinic, University of Barcelona, IDIBAPS, CIBERSAM, Institute of Neuroscience, Barcelona, Catalonia, Spain;3. Department of Mental Health, AUSL Umbria 2, Terni, Italy;1. Universidade Federal do Paraná, Av. Lothário Meissner, 632, Jardim Botânico, CEP 80210-170, Curitiba, PR, Brazil;2. Embrapa Uva e Vinho, Rua Livramento, 515, Caixa Postal 130, CEP 95700-000, Bento Gonçalves, RS, Brazil |
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| Abstract: | 1,2:5,6-Di-O-isopropylidene-D-glucitol was converted via its 1,4-dimethanesulfonate into the 1-azido-4-methanesulfonate which, after deprotection and treatment with barium hydroxide, afforded a 9:1 mixture of the corresponding 3,4- and 4,5-anhydro derivatives. Reduction of this mixture by transfer hydrogenation using ammonium formate in methanol and Pd/C as catalyst afforded 1,4-dideoxy-1,4-imino-D-glucitol (4), the structure of which was proved after acetylation by 1H-n.m.r. spectroscopy. Compound 4 is a potent alpha-D-glucosidase inhibitor (Ki 7 X 10(-4)M) and a less potent beta-D-glucosidase inhibitor (Ki 1.25 X 10(-4)M), and inhibits beta-D-galactosidase non-competitively. |
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