作为己糖胺酶抑制剂的2-乙酰氨基-1,2-二脱氧野尻霉素-赖氨酸杂合物
2-Acetamino-1,2-dideoxynojirimycin-lysine hybrids as hexosaminidase inhibitors.
作者信息
Steiner Andreas J, Schitter Georg, Stütz Arnold E, Wrodnigg Tanja M, Tarling Chris A, Withers Stephen G, Mahuran Don J, Tropak Michael B
机构信息
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
出版信息
Tetrahedron Asymmetry. 2009 May 1;20(6-8):832-835. doi: 10.1016/j.tetasy.2009.02.015.
Abstract
Cyclisation by double reductive amination of 2-acetamino-2-deoxy-D-xylo-hexos-5-ulose with N-2 protected L-lysine derivatives provided 2-acetamino-1,2-dideoxynojirimycin derivatives without any observable epimer formation at C-5. Modifications on the lysine moiety gave access to lipophilic derivatives that exhibited improved hexosaminidase inhibitory activities.
摘要
通过2-乙酰氨基-2-脱氧-D-木糖-己糖-5-酮与N-2保护的L-赖氨酸衍生物的双还原胺化反应进行环化，得到了2-乙酰氨基-1,2-二脱氧野尻霉素衍生物，且在C-5位没有观察到任何差向异构体的形成。对赖氨酸部分进行修饰可得到亲脂性衍生物，这些衍生物表现出改善的己糖胺酶抑制活性。
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2
Sphingolipids-Their Metabolic Pathways and the Pathobiochemistry of Neurodegenerative Diseases.鞘脂类——它们的代谢途径与神经退行性疾病的病理生物化学
Angew Chem Int Ed Engl. 1999 Jun 1;38(11):1532-1568. doi: 10.1002/(SICI)1521-3773(19990601)38:11<1532::AID-ANIE1532>3.0.CO;2-U.
3
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6
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