SOLID PHASE OLIGOSACCHARIDE SYNTHESIS

SOLID PHASE OLIGOSACCHARIDE SYNTHESIS
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固相低聚糖合成

DOI:
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发表时间:
2002
期刊:
影响因子:
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通讯作者:
P. Seeberger
P. Seeberger
中科院分区:
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作者:
P. Seeberger

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多糖是结构上最复杂的主要类别的生物聚合物。虽然核酸和蛋白质是线性组装体,但多糖在结构和立体化学上更多样化。通过形成糖缀合物如糖脂和糖蛋白,给多糖结构增加了额外的复杂性。以糖缀合物形式存在的寡聚体介导多种事件,包括炎症、免疫应答、转移和受精。细胞表面碳水化合物作为各种肿瘤的生物标记物,并作为其他物质(包括病原体)的结合位点。对低聚糖和糖复合物在维持生命的基本过程中所起的重要作用的认识日益加深,刺激了对获得可用数量的这些材料的需求。糖缀合物通常以微不均匀混合物的形式存在,并且难以以均匀形式分离,因此仅产生少量的所需物质。与自然资源隔离有关的问题为化学合成提供了机会。合成碳水化合物化学的发展集中在寻找两个重要挑战的解决方案上:需要区分每个单糖上包含的相似官能团(羟基或氨基),以及需要诱导选择性形成各种糖苷键。与其他两类重复生物聚合物中发现的键不同,在不断增长的寡糖系综中形成的每个糖苷键构成了一个新的立体发生位点。关于-
Polysaccharides are the structurally most complex of the major classes of biopolymers. While nucleic acids and proteins are linear assemblies, polysaccharides are structurally and stereochemically more diverse. Additional complexity is added to the polysaccharide structure by the formation of glycoconjugates such as glycolipids and glycoproteins. Oligosaccharides in the form of glycoconjugates mediate a variety of events, including inflammation, immunological response, metastasis, and fertilization. Cell surface carbohydrates act as biological markers of various tumors and as binding sites for other substances, including pathogens. The increased understanding of the important roles oligosaccharides and glycoconjugates play in fundamental life-sustaining processes has stimulated a need for access to usable quantities of these materials. Glycoconjugates commonly exist as microheterogeneous mixtures and are difficult to isolate in homogeneous form, therefore yielding only small amounts of the desired material. The problems associated with isolation from natural sources give rise to opportunities for chemical synthesis. The developments in synthetic carbohydrate chemistry have centered on finding solutions to two important challenges: the need to differentiate similar functionality (hydroxyl or amino) contained on each monosaccharide and the need to induce the selective formation of a variety of glycosidic linkages. Unlike linkages found in the other two classes of repeating biopolymers, each glycosidic bond to be fashioned in a growing oligosaccharide ensemble constitutes a new locus of stereogenicity. In re-
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