Synthesis of the Oligosaccharides of Burkholderia pseudomallei and B. mallei Capsular Polysaccharide and Preliminary Immunological Studies of Their Protein Conjugates.,The Journal of Organic Chemistry

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Synthesis of the Oligosaccharides of Burkholderia pseudomallei and B. mallei Capsular Polysaccharide and Preliminary Immunological Studies of Their Protein Conjugates.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-22 , DOI: 10.1021/acs.joc.9b03085
Xueyun Geng ₁ , Guirong Wang ₁ , Zhongwu Guo ₂ , Guofeng Gu ₁

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Efficient strategies were developed for the synthesis of 6-deoxy-d-manno-heptopyranose and its β-(1 → 3)-linked oligomers as fragments of the common and major capsular polysaccharide, type I O-PS, of Burkholderia pseudomallei and Burkholderia mallei. The unusual heptose was synthesized from mannose, highlighted by the facile Wittig reaction and anti-Markovnikov hydroboration of the resultant olefin. The difficult β-mannosidic linkage in the oligosaccharides was achieved in high stereoselectivity by H-bond-mediated aglycone delivery. All of the oligosaccharides were conjugated with the carrier protein CRM197. Preliminary immunological evaluations of the resultant glycoconjugates in mice verified their efficacy to elicit high titers of immunoglobulin G antibodies and robust T-cell-dependent immune responses. It was also found that the trisaccharide conjugates provoked the strongest immune responses, worthy of further in-depth study for vaccine development.

中文翻译：

Burkholderia pseudomallei和B. Mallei荚膜多糖的寡糖的合成及其蛋白缀合物的初步免疫学研究。

为合成6-脱氧-d-甘露聚糖-七吡喃糖及其β-（1→3）-连接的寡聚体，作为伯克霍尔德氏菌和假伯克霍尔德氏菌的常见和主要荚膜多糖I O-PS的片段，开发了有效的策略马莱。不寻常的庚糖是由甘露糖合成的，突出之处在于得到的烯烃易于进行的Wittig反应和抗Markovnikov硼氢化反应。通过H键介导的糖苷配基的高立体选择性实现了寡糖中困难的β-甘露糖苷键。所有的寡糖都与载体蛋白CRM197缀合。小鼠中产生的糖缀合物的初步免疫学评估证实了它们诱导高滴度的免疫球蛋白G抗体和强大的T细胞依赖性免疫反应的功效。

更新日期：2020-01-23

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