在真菌细菌细胞壁上合成多可萨糖胺阿拉比南基因的合成
Akihiro Ishiwata1, Yukishige Ito
1RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. aishiwa@riken.jp
Journal of the American Chemical Society
|February 4, 2011
概括
研究人员合成了真菌细菌细胞壁的关键成分,一种β-阿拉比诺 (β-Araf) 糖. 这一成就简化了复杂的真菌菌素多糖的产生,如阿拉比诺 (AG) 和利波阿拉比诺 (LAM).
科学领域:
- 碳水化合物化学 碳水化合物化学
- 合成有机化学 合成有机化学
- 葡萄糖生物学 葡萄糖生物学
- 微生物细胞壁的合成
背景情况:
- 菌根菌的阿拉比南是Mycobacterium物种细胞壁中的关键结构元素.
- 阿拉比南是必不可少的菌根细胞壁多糖的常见成分,包括阿拉比诺 (AG) 和利波阿拉比诺南 (LAM).
- 了解和合成这些结构对于开发新的抗菌菌疗法至关重要.
研究的目的:
- 为了实现含有多糖的β-阿拉比诺 (β-Araf) 的合成,它代表了在真菌细菌细胞壁中发现的常见的阿拉比诺基基因.
- 开发一种适用于构建更复杂的真菌细菌细胞壁糖的多功能合成策略.
主要方法:
- 立体选择性β-阿拉比诺氨基化被采用受保护的阿拉比诺氨基素捐赠体 (3,5-O-TIPDS和NAP受保护) 用于分子间糖化和分子内亚格利康输送 (IAD).
- 采用了融合碎片合方法,涉及线性连接的分支碎片.
- 硫糖化物捐赠者是从三步程序中的乙胺保护碎片中准备的,以促进高效的碎片组装.
主要成果:
- 已经成功合成了菌根性阿拉比南的多科萨沙克里德基因 (22 个阿拉夫单位).
- 开发的战略证明了有效的立体选择性糖化和碎片合.
- 合成方法可以将各种保护组和碎片类型纳入.
结论:
- 已建立的合成策略为构建复杂的mycobacterial arabinans提供了一个强大的方法.
- 这项工作为合成更大,更复杂的真菌细菌细胞壁组件奠定了基础,包括阿拉比诺和阿拉比诺.
- 该方法很容易适应合成来自细胞壁的多种真菌细菌甘.
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