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Synthesis of Neoglycoconjugates Containing 4-Amino-4-deoxy-l-arabinose Epitopes Corresponding to the Inner Core of Burkholderia and Proteus Lipopolysaccharides

机译:含有与伯克霍尔德菌和变形杆菌脂多糖内核相对应的4-氨基-4-脱氧-1-阿拉伯糖表位的新糖缀合物的合成

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摘要

Disaccharides that contain 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) and d-glycero-d-talo-oct-2-ulosonic acid (Ko) substituted at the 8-position by 4-amino-4-deoxy-β-l-arabinopyranosyl (Ara4N) residues have been prepared. Coupling an N-phenyltrifluoroacetimidate-4-azido-4-deoxy-l-arabinosylglycosyl donor to acetyl-protected allyl glycosides of Kdo and Ko afforded anomeric mixtures of disaccharide products in 74 and 90 % yield, respectively, which were separated by chromatography. Further extension of an intermediate Ara4N-(1→8)-Kdo disaccharide acceptor, which capitalized on a regioselective glycosylation with a Kdo bromide donor under Helferich conditions, afforded the branched trisaccharide α-Kdo-(2→4)[β-l-Ara4N-(1→8)]-α-Kdo derivative. Deprotection of the protected di- and trisaccharide allyl glycosides was accomplished by TiCl4-promoted benzyl ether cleavage followed by the removal of ester groups and reduction of the azido group with thiol or Staudinger reagents, respectively. The reaction of the anomeric allyl group with 1,3-propanedithiol under radical conditions afforded the thioether-bridged spacer glycosides, which were efficiently coupled to maleimide-activated bovine serum albumin. The neoglycoconjugates serve as immunoreagents with specificity for inner core epitopes of Burkholderia and Proteus lipopolysaccharides.
机译:包含在3-位被4-氨基-4取代的3-脱氧-d-甘露聚糖-辛-2-氟酸(Kdo)和d-甘油-d-talo-辛-2-氟酸(Ko)的二糖已经制备了-脱氧-β-1-芳基吡喃糖基(Ara4N)残基。将N-苯基三氟乙酰亚氨酸酯-4-叠氮基-4-脱氧-1-阿拉伯糖基糖基供体与Kdo和Ko的乙酰基保护的烯丙基糖苷偶联,分别得到二糖产物的端基异构体混合物,产率为74%和90%,通过色谱法分离。中间体Ara4N-(1→8)-Kdo二糖受体的进一步延伸,利用在Helferich条件下与溴化Kdo供体进行区域选择性糖基化,得到了支链三糖α-Kdo-(2→4)[β-1- Ara4N-(1→8)]-α-Kdo衍生物。被保护的二糖和三糖烯丙基糖苷的脱保护是通过TiCl4促进的苄基醚裂解,然后分别用硫醇或Staudinger试剂除去酯基并还原叠氮基。异头烯丙基与1,3-丙二硫醇在自由基条件下的反应提供了硫醚桥连的间隔糖苷,其与马来酰亚胺活化的牛血清白蛋白有效偶联。新糖缀合物用作对伯克霍尔德氏菌和变形杆菌脂多糖的内核表位具有特异性的免疫试剂。

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