De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction
De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction
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DOI：
10.1002/anie.200701354
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发表时间：
2007-01-01
影响因子：
16.6
通讯作者：
O'Doherty, George A.
中科院分区：
文献类型：
--
作者：
Guo, Haibing;O'Doherty, George A.
炭疽病是一种人畜共患疾病，由孢子形成细菌炭疽杆菌引起。[1]炭疽芽孢杆菌属于芽孢杆菌科，其由不同的细菌群组成，所有细菌都形成内生孢子。[2]炭疽杆菌是该属中最重要的成员，被认为是一种有效的生物战剂。它的保护性多肽胶囊由聚-d-谷氨酸组成，抑制吞噬作用。[3]最近，从胶囊中分离出由三种l-鼠李糖和一种稀有糖d-蒽糖组成的四糖（方案1）。[4]蒽糖的独特性和碳水化合物结构对进化变化的抵抗力使炭疽四糖1成为炭疽检测和疫苗开发的有趣目标。[5]最近，有两种以碳水化合物为基础的炭疽四糖和一种相关三糖的合成方法被报道。[6]在这些途径中，立体化学来自已知但不太常见的糖l-鼠李糖（2）和罕见的d-岩藻糖（3）。与这些传统的方法相比，我们一直在研究从头不对称的方法，单，双，和寡糖。[7]在此我们
Anthrax is a zoonotic disease caused by the spore-forming bacterium Bacillus anthracis.[1] Bacillus anthracis belongs to the family Bacillaceae, which consists of a diverse group of bacteria, all of which form endospores.[2] Bacillus anthracis is the most important member of this genus and is considered to be a potent agent for biological warfare. Its protective polypeptide capsule consists of poly-d-glutamic acid, which inhibits phagocytosis.[3] Recently, a tetrasaccharide made up of three l-rhamnose sugars and a rare sugar, d-anthrose, was isolated from the capsule (Scheme 1).[4] The uniqueness of the anthrose sugar and the resistance of carbohydrate structures to evolutionary change make the anthrax tetrasaccharide 1 an interesting target for anthrax detection and vaccine development.[5] Thus, synthetic access to this tetrasaccharide is desired.Recently, two carbohydrate-based approaches to the anthrax tetrasaccharide and one to a related trisaccharide have been reported.[6] In these routes the stereochemistry is derived from the known but less common sugar l-rhamnose (2) and the rare d-fucose (3). In contrast to these traditional approaches, we have been investigating de novo asymmetric approaches to mono, di-, and oligosaccharides.[7] Herein we