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Diastereoselective One-Step Synthesis of 2-Keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN) Analogues as Templates for the Development of Influenza Drugs

文献类型： 外文期刊

作者： Laborda, Pedro 1 ; Wang, Su-Yan 1 ; Lu, Ai-Min 3 ; He, Meng 1 ; Duan, Xu-Chu 1 ; Qian, Ying-Juan 3 ; Jung, Yong-Sam 4 ; L 1 ;

作者机构： 1.Nanjing Agr Univ, Coll Food Sci & Technol, Glyc & Glycan Bioengn Res Ctr, Nanjing 210095, Jiangsu, Peoples R China

2.Jiangsu Acad Agr Sci, Nanjing 210014, Jiangsu, Peoples R China

3.Nanjing Agr Univ, Coll Sci, Nanjing 210095, Jiangsu, Peoples R China

4.Nanjing Agr Univ, Dept Vet Med, Antiviral Unit, Nanjing 210095, Jiangsu, Peoples R China

关键词： aldol reaction;antiviral agents;diastereoselectivity;KDN;2-keto-3-deoxy-D-glycero-D-galacto-nononic acid;sialic acids

期刊名称：ADVANCED SYNTHESIS & CATALYSIS （ 影响因子：5.837； 五年影响因子：5.112 ）

ISSN：

年卷期：

页码：

收录情况： SCI

摘要： Novel sialic acid scaffolds have great significance in the development of influenza neuraminidase inhibitors. Here the enzymatic synthesis of a wide range of 2-keto-3-deoxy-d-glycero-d-galacto-nononic acid (KDN) analogues via aldol addition of pyruvate to d-mannose, d-glucose, d-galactose, 2-deoxy-d-glucose, d-arabinose, l-arabinose and l-rhamnose using a previously unstudied N-acetylneuraminic acid (Neu5Ac) aldolase derived from the bacterium Dyadobacter fermentas is exemplified. Several of the synthesized KDN analogues showed comparable or better inhibitory activity than unstudied Neu5Ac against the mutated influenza neuraminidases (A/California/04/2009 and A/Anhui/1/2005), which both show resistance to Neu5Ac-based neuraminidase inhibitors, demonstrating that these compounds are promising templates for the development of anti-influenza drugs.

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