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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.

DOI:10.1016/j.tetasy.2009.02.015
PMID:22328804
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3276585/
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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1
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Angew Chem Int Ed Engl. 1999 Mar 15;38(6):750-770. doi: 10.1002/(SICI)1521-3773(19990315)38:6<750::AID-ANIE750>3.0.CO;2-6.
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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4
Identification of pharmacological chaperones for Gaucher disease and characterization of their effects on beta-glucocerebrosidase by hydrogen/deuterium exchange mass spectrometry.戈谢病药理伴侣分子的鉴定及其对β-葡萄糖脑苷脂酶影响的氢/氘交换质谱表征
Chembiochem. 2008 Nov 3;9(16):2650-62. doi: 10.1002/cbic.200800304.
5
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Bioorg Med Chem Lett. 2008 Mar 15;18(6):1922-5. doi: 10.1016/j.bmcl.2008.01.124. Epub 2008 Feb 7.
6
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Nature. 2007 May 3;447(7140):92-6. doi: 10.1038/nature05746. Epub 2007 Apr 22.
7
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Carbohydr Res. 2007 Sep 3;342(12-13):1850-8. doi: 10.1016/j.carres.2007.03.024. Epub 2007 Mar 28.
8
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Chem Biol. 2007 Feb;14(2):153-64. doi: 10.1016/j.chembiol.2006.12.006.
9
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J Biol Chem. 2007 Mar 23;282(12):9150-61. doi: 10.1074/jbc.M609304200. Epub 2007 Jan 21.
10
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Biochim Biophys Acta. 2006 Dec;1758(12):2057-79. doi: 10.1016/j.bbamem.2006.05.027. Epub 2006 Jun 14.