Synthesis of a pyruvylated N-acetyl-β-D-mannosamine containing disaccharide repeating unit of a cell wall glycopolymer from Paenibacillus alvei
Synthesis of a pyruvylated N-acetyl-β-D-mannosamine containing disaccharide repeating unit of a cell wall glycopolymer from Paenibacillus alvei
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DOI：
10.24820/ark.5550190.p011.358
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发表时间：
2021-01-01
期刊：
影响因子：
0.9
通讯作者：
Kosma, Paul
中科院分区：
文献类型：
--
作者：
Krauter, Simon;Schaeffer, Christina;Kosma, Paul
通过将受保护的N-乙酰氨基葡萄糖受体与吡喃葡萄糖供体糖基化，生成β-(1->；4)-键，制备了一种与细菌表层蛋白锚定在次生细胞壁糖共聚物上的二糖。然而，随后构型的反转和用三氟酸酐在位置2引入叠氮化物导致了四唑衍生物的形成。或者，叠氮化钠置换2-O-甲磺酸，还原和N-乙酰化使其转化为远端的N-乙酰-β-D-甘露糖胺残基。后一单元的丙酮基化和全局去保护使来自肺泡状芽孢杆菌的二糖重复单元成为结晶学和结合研究的配体。
A disaccharide implicated in anchoring of bacterial Surface-layer proteins to secondary cell wall glycopolymers has been prepared by glycosylation of a protected N-acetyl glucosamine acceptor with a glucopyranosyl donor to generate the beta-(1 -> 4)-linkage. Subsequent inversion of the configuration and azide introduction at position 2 with triflic anhydride, however, led to formation of a tetrazole derivative. Alternatively, displacement of a 2-O-mesylate by sodium azide, reduction and N-acetylation enabled the conversion into the distal N-acetyl-beta-D-mannosamine residue. Pyruvylation of the latter unit and global deprotection afforded the disaccharide repeating unit from Paenibacillus alvei as a ligand for crystallographic and binding studies.[GRAPHICS].