2,4-Diamino-2,4,6-trideoxyglucose (bacillosamine) is a monosaccharide found in many pathogenic bacteria, variation in the functionalities appended to the amino groups occurs depending on the species the sugar is derived from. We here report the first synthesis of bacillosamine synthons that allow for the incorporation of two different functionalities at the C-2-N-acetyl and C-4-amines. We have developed chemistry to assemble a set of conjugation ready Neisseria meningitidis C-2-N-acetyl bacillosamine saccharides, carrying either an acetyl or (R)- or (S)-glyceroyl at the C-4 amine. The glyceroyl bacillosamines have been further extended at the C-3-OH with an α-D-galactopyranose to provide structures that occur as post-translational modifications of N. meningitidis PilE proteins, which make up the bacterial pili.

中文翻译：

---

正交保护和功能化细菌素的合成

2,4-二氨基-2,4,6-三脱氧葡萄糖（bacillosamine）是在许多致病细菌中发现的单糖，取决于糖的来源种类，氨基上附加的官能团会发生变化。我们在这里报道了杆菌胺合成子的首次合成，其允许在C-2- N-乙酰基和C-4-胺上引入两种不同的功能。我们已经开发出化学方法来组装一套易于结合的脑膜炎奈瑟氏球菌C-2- N-乙酰基杆菌胺糖，在C-4胺上带有乙酰基或（R）-或（S）-甘油酰。甘油酰杆菌胺已在C-3-OH处用α- D进一步延伸-半乳糖吡喃糖提供的结构是脑膜炎奈瑟氏菌PilE蛋白的翻译后修饰，构成细菌菌毛。