Synthesis of a Pentasaccharide Fragment Related to the Inner Core Region of Rhizobial and Agrobacterial Lipopolysaccharides.
Synthesis of a Pentasaccharide Fragment Related to the Inner Core Region of Rhizobial and Agrobacterial Lipopolysaccharides.
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DOI：
10.1021/acs.joc.7b02172
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发表时间：
2017-12-01
期刊：
影响因子：
--
通讯作者：
Kosma P
中科院分区：
文献类型：
--
作者：
Trattnig N;Farcet JB;Gritsch P;Christler A;Pantophlet R;Kosma P
通过单糖构建块的顺序组装，制备了带有3-氨基丙基间隔段的五糖片段α-d-Man-(1→5)-[α-d-Kdo-(2→4)-]α-d-Kdo-(2→6)-β-d- glcnac -(1→6)-α-d- glcnac。采用1,3-恶唑啉给体合成葡萄糖胺二糖，作为细菌脂质a区的骨架替代物，随后与异丙基保护的氯氟给体偶联，得到受保护的四糖中间体。最后，使用一个正交保护的甘露配置的三氯乙酸酯供体，以良好的收率实现了Kdo的5-OH基的立体糖基化。所得到的五糖在末端甘露糖的3、4和6位被适当地保护以进一步延长链。全局脱保护使目标五糖可用于转化为新糖缀合物和“可点击”配体。
The pentasaccharide fragment α-d-Man-(1 → 5)-[α-d-Kdo-(2 → 4)-]α-d-Kdo-(2 → 6)-β-d-GlcNAc-(1 → 6)-α-d-GlcNAc equipped with a 3-aminopropyl spacer moiety was prepared by a sequential assembly of monosaccharide building blocks. The glucosamine disaccharide—as a backbone surrogate of the bacterial lipid A region—was synthesized using an 1,3-oxazoline donor, which was followed by coupling with an isopropylidene-protected Kdo-fluoride donor to afford a protected tetrasaccharide intermediate. Eventually, an orthogonally protected manno-configured trichloroacetimidate donor was used to achieve the sterically demanding glycosylation of the 5-OH group of Kdo in good yield. The resulting pentasaccharide is suitably protected for further chain elongation at positions 3, 4, and 6 of the terminal mannose. Global deprotection afforded the target pentasaccharide to be used for the conversion into neoglycoconjugates and “clickable” ligands.
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影响因子：
4.8
作者：
Kanipes, MI;Ribeiro, AA;Raetz, CRH
通讯作者：
Raetz, CRH
影响因子：
1.8
作者：
IMOTO, M;KUSUNOSE, N;SHIBA, T
通讯作者：
SHIBA, T
影响因子：
4
作者：
FUKASE, K;KAMIKAWA, T;KUSUMOTO, S
通讯作者：
KUSUMOTO, S
DOI：
10.1007/978-3-7091-0733-1_3
发表时间：
2011-01-01
期刊：
BACTERIAL LIPOPOLYSACCHARIDES: STRUCTURE, CHEMICAL SYNTHESIS, BIOGENESIS AND INTERACTION WITH HOST CELLS
影响因子：
--
作者：
Knirel, Yuriy A.
通讯作者：
Knirel, Yuriy A.
影响因子：
5.4
作者：
Doores, Katie J.;Huber, Michael;Burton, Dennis R.
通讯作者：
Burton, Dennis R.