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Study of Microwave Effects for Syntheses of Oligosaccharides and Glycopeptides

微波效应合成低聚糖和糖肽的研究

基本信息

批准号：
18580109
负责人：
SHIMIZU Hiroki
金额：
$ 2.53万
依托单位：
National Institute of Advanced Industrial Science and Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2006
资助国家：
日本
起止时间：
2006 至 2007
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-18580109/
关键词：
Oligosaccharide Organic Chemistry Microwave Green Chemistry Electromagnetic Wave Glycopeptide

项目摘要

Although microwave has been applied for chemical reactions, especially as an effective heating tool, we have had some hints that microwaves could also bring nonthermal effects through, studying three of carbohydrate-related synthetic studies.1) Glycosylation using methyl glycoside donor : Methyl glycosides are very stable compounds and easy to be prepared and easy to be handled, but they were not suitable as glycosyl donors because the conditions to activate methoxy group could also cut C-O bond off in sugar ring. Nevertheless this background, methyl glycosides could behave as glycosyl donors under microwave irradiation with Lewis acids. Transglycosylation from methyl to octyl was performed in 88% yield.2) Microwave irradiation at low temperatures to synthesize Lewis X oligosaccharide : Galactosylation onto 4-OH in a fucosyl glucosamine accepted has not achieved without microwave support, which yielded only side reactions and byproducts, namely cleavage of the fucosyl bond, nucleophili … More c reactions by methylthio group and so on. Nevertheless this background, microwave irradiation at low temperature gave fruitful result.3) Microwaves accelerated glycopeptide synthesis : In our experiment as coupling of a threonine having acetylated Core2 trisaccharide to an alanine onto Tenta gel resin, warming up to 50℃ by pulsed microwave irradiation pushed up to 98% yield while the reaction in the same temperature by conventional heating gave only 93% yield. Based on these preliminary experiments, we synthesized the MUC1 repeating unit which consisted of twenty of amino acid residues with five of acetylated Core2 trisaccharides. Microwave led fourteen times faster preparation or three times higher yield.4) Other than above, we have studied for development of immobilized reagents, microwave effects for enzyme reactions and related cyclodextrin effects basical study for gold-nanoparticle supported oligosaccharide syntheses and development of glycopeptide reactor using microwave irradiation effectively. Less

虽然微波已经被应用于化学反应，特别是作为一种有效的加热工具，但我们通过研究三个与碳水化合物相关的合成研究，得到了一些暗示，微波也可以带来非热效应。1）使用甲基糖苷供体的糖基化：甲基糖苷是非常稳定的化合物，易于制备和处理，但由于甲氧基的活化条件也会切断糖环上的C-O键，因此不适合作为糖基供体。尽管如此，甲基糖苷可以在微波辐射下与刘易斯酸作为糖基供体。2）低温微波辐射合成刘易斯X寡糖：岩藻糖基氨基葡萄糖经4-羟基半乳糖基化反应在没有微波支持的情况下无法实现，这只会产生副反应和副产物，即岩藻糖基键的断裂，亲核试剂的生成，以及糖基化反应的发生。 ...更多信息 c通过甲硫基等进行反应。尽管如此，在低温下微波辐射还是取得了丰硕的成果。3）微波加速糖肽合成：在我们的实验中，将具有乙酰化的Core 2三糖的苏氨酸偶联到Tenta凝胶树脂上的丙氨酸上，通过脉冲微波辐射升温至50℃，产率可达98%，而在相同温度下通过常规加热反应，产率仅为93%。基于这些初步实验，我们合成了MUC 1重复单元，其由20个氨基酸残基和5个乙酰化的Core 2三碱基组成。4）除此之外，我们还研究了固定化试剂的开发、微波对酶反应的影响及相关的环糊精效应、纳米金负载寡糖合成的基础研究和微波辐射下糖肽反应器的开发。少