Chemical Synthesis and Application of Biotinylated Oligo-α-(1 → 3)-d-Glucosides To Study the Antibody and Cytokine Response against the Cell Wall α-(1 → 3)-d-Glucan of Aspergillus fumigatus.
Chemical Synthesis and Application of Biotinylated Oligo-α-(1 → 3)-d-Glucosides To Study the Antibody and Cytokine Response against the Cell Wall α-(1 → 3)-d-Glucan of Aspergillus fumigatus.
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DOI：
10.1021/acs.joc.8b01142
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发表时间：
2018-11-02
期刊：
影响因子：
--
通讯作者：
Nifantiev NE
中科院分区：
文献类型：
--
作者：
Komarova BS;Wong SSW;Orekhova MV;Tsvetkov YE;Krylov VB;Beauvais A;Bouchara JP;Kearney JF;Aimanianda V;Latgé JP;Nifantiev NE
首次采用分块合成法合成了α-（1 → 3）-d-葡聚糖（Aspergillus fumigatus）细胞壁的主要成分之一）的七、九、十一碳-α-（1 → 3）-d-葡糖苷。α-（1 → 3）-d-葡聚糖链的会聚组装是通过与带有6-O-苯甲酰基的低聚葡萄糖苷衍生物的糖基化实现的。这些基团能够远程参与α-立体控制，即使在大糖基供体的情况下，也使它们成为有效的α-定向工具。合成的生物素化寡聚葡糖苷（以及先前合成的三-和五-α-（1 → 3）-d-葡糖苷的生物素化衍生物）被抗α-（1 → 3）-葡聚糖人多克隆抗体更好地识别，并且在刺激人外周血单核细胞时诱导的细胞因子应答高于其天然对应物α-（1 → 3）-d-葡聚糖，固定在常规微量滴定板上。与天然α-（1 → 3）-葡聚糖的随机吸附相比，通过链霉亲和素-生物素对连接配备有亲水性间隔基的合成寡糖，可实现更好的空间呈现和负载控制。寡糖苷长度的增加导致其更好的识别和细胞因子产生的增强。因此，使用合成的α-（1 → 3）-葡聚糖寡糖，我们开发了一种比基于天然α-（1 → 3）-葡聚糖的测定法更灵敏的宿主免疫应答测定法。
Biotinylated hepta-, nona- and undeca-α-(1 → 3)-d-glucosides representing long oligosaccharides of α-(1 → 3)-d-glucan, one of the major components of the cell walls of the fungal pathogen Aspergillus fumigatus, were synthesized for the first time via a blockwise strategy. Convergent assembly of the α-(1 → 3)-d-glucan chains was achieved by glycosylation with oligoglucoside derivatives bearing 6-O-benzoyl groups. Those groups are capable of remote α-stereocontrolling participation, making them efficient α-directing tools even in the case of large glycosyl donors. Synthetic biotinylated oligoglucosides (and biotinylated derivatives of previously synthesized tri- and penta-α-(1 → 3)-d-glucosides) loaded on streptavidin microtiter plates were shown to be better recognized by anti-α-(1 → 3)-glucan human polyclonal antibodies and to induce higher cytokine responses upon stimulation of human peripheral blood mononuclear cells than their natural counterpart, α-(1 → 3)-d-glucan, immobilized on a conventional microtiter plate. Attachment of the synthetic oligosaccharides equipped with a hydrophilic spacer via the streptavidin–biotin pair allows better spatial presentation and control of the loading compared to the random sorption of natural α-(1 → 3)-glucan. Increase of oligoglucoside length results in their better recognition and enhancement of cytokine production. Thus, using synthetic α-(1 → 3)-glucan oligosaccharides, we developed an assay for the host immune response that is more sensitive than the assay based on native α-(1 → 3)-glucan.
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Dectin-1介导β-葡聚糖的生物学作用。
DOI：
10.1084/jem.20021890
发表时间：
2003-05-05
期刊：
The Journal of experimental medicine
影响因子：
--
作者：
Brown GD;Herre J;Williams DL;Willment JA;Marshall AS;Gordon S
通讯作者：
Gordon S
影响因子：
1.8
作者：
Komarova, Bozhena S.;Tsvetkov, Yury E.;Nifantiev, Nikolay E.
通讯作者：
Nifantiev, Nikolay E.
影响因子：
4.4
作者：
Bozza, Silvia;Clavaud, Cecile;Romani, Luigina
通讯作者：
Romani, Luigina
影响因子：
4.3
作者：
Komarova, Bozhena S.;Orekhova, Maria V.;Nifantiev, Nikolay E.
通讯作者：
Nifantiev, Nikolay E.
影响因子：
2
作者：
Ustyuzhanina, N;Komarova, B;Nifantiev, N
通讯作者：
Nifantiev, N