Low-Concentration 1,2-trans β-Selective Glycosylation Strategy and ItsApplications in Oligosaccharide Synthesis

Chin-Sheng Chao; Chen-Wei Li; Min-Chun Chen; Shih-Sheng Chang; Kwok-Kong Tony Mong

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Low-Concentration 1,2-trans β-Selective Glycosylation Strategy and ItsApplications in Oligosaccharide Synthesis

机译：低浓度1,2-反式β-选择性糖基化策略及其在寡糖合成中的应用

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This study develops an op-erationally easy, efficient, and general1,2-trans β-selective glycosylation reac-tion that proceeds in the absence of aC2 acyl function. This process employschemically stable thioglycosyl donorsand low substrate concentrations toachieve excellent β-selectivities in gly-cosylation reactions. This method iswidely applicable to a range of glycosyl substrates irrespective of their struc-tures and hydroxyl-protecting func-tions. This low-concentration 1,2-transβ-selective glycosylation in carbohy-drate chemistry removes the restrictionof using highly reactive thioglycosidesto construct 1,2-trans β-glycosidicbonds. This is beneficial to the designof new strategies for oligosaccharidesynthesis, as illustrated in the prepara-tion of the biologically relevant (3-(1—6)-glucan trisaccharide, β-linked Gb_3and isoGb_3

机译：这项研究开发了一种操作简便，有效且通用的1,2-反式β-选择性糖基化反应，该反应在不存在αC2酰基功能的情况下进行。该方法采用化学上稳定的硫糖基供体和低底物浓度，从而在糖基化反应中获得出色的β选择性。该方法广泛适用于各种糖基底物，无论其结构和羟基保护功能如何。碳酸盐化学中的这种低浓度的1,2-反式β-选择性糖基化消除了使用高反应性硫代糖苷构建1,2-反式β-糖苷键的限制。这有利于寡糖合成新策略的设计，如生物学相关的3-（1-6）-葡聚糖三糖，β-连接的Gb_3和isoGb_3的制备所示

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来源
《Chemistry: A European journal》 |2009年第41期|共11页
作者
Chin-Sheng Chao; Chen-Wei Li; Min-Chun Chen; Shih-Sheng Chang; Kwok-Kong Tony Mong;
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正文语种 eng
中图分类应用化学;
关键词
carbohydrates; glycosy-lation; neighboring-group effects; stereoselectivity; substrate concen-tration;

机译：碳水化合物;糖基化;相邻基团效应;立体选择性;底物浓度;

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1. Low-Concentration 1,2-trans β-Selective Glycosylation Strategy and ItsApplications in Oligosaccharide Synthesis [J] . Chin-Sheng Chao, Chen-Wei Li, Min-Chun Chen, Chemistry: A European journal . 2009,第41期

机译：低浓度1,2-反式β-选择性糖基化策略及其在寡糖合成中的应用
2. 1,2-trans Glycosylation via Neighboring Group Participation of 2-O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis [J] . Karak Milandip, Joh Yohei, Suenaga Masahiko, Organic letters . 2019,第4期

机译：通过相邻群体参与2-O-烷氧基甲基的1,2-反式糖基化：应用于单盆寡糖合成
3. New strategies for the synthesis of bio-medically relevant oligosaccharides: Recent updates on 1,2-cis-O-Glycosylation and α-O-Sialylation [J] . Crotti S., Adamo R. Current Organic Synthesis . 2013,第4期

机译：合成生物医学相关寡糖的新策略：1,2-顺式-O-糖基化和α-O-唾液酸化的最新进展
4. A NOVEL SYNTHETIC APPROACH TOWARD DIVERSE p-GLYCEROGLYCOLIPIDS BASED ON A NEIGHBORING FREE 1,2-trans-SELECTIVE GLYCOSYLATION [C] . Nahoko Yagami, Akihiro Imamura, Hideharu Ishida International Carbohydrate Symposium . 2018

机译：基于相邻自由1,2-反式选择性糖基化的一种新型P-甘油基哌普体的一种新型合成方法
5. Chapter 1. Total synthesis of Fumonisin B1. Chapter 2. Synthesis of Unnatural Sphingolipids: 1-deoxy-5-hydroxysphinganine and its diastereomers. Chapter 3. Development of Methodology: Synthesis of cis- and trans-homoallylic alcohols. Chapter 4. Human Milk Oligosaccharides: Synthesis of Natural and Unnatural oligomers [D] . Pereira, Claney L. 2010

机译：第1章。伏马毒素B1的全合成。第二章。非天然鞘脂的合成：1-脱氧-5-羟基鞘氨醇及其非对映异构体。第3章方法的发展：顺式和反式均烯丙基醇的合成。第4章人乳寡糖：天然和非天然低聚物的合成
6. Synthetic glycosylation of proteins using N-(beta-saccharide) iodoacetamides: applications in site-specific glycosylation and solid-phase enzymic oligosaccharide synthesis. [O] . S Y Wong, G R Guile, R A Dwek, 1994

机译：使用N-（β-糖）碘乙酰胺的蛋白质合成糖基化：在位点特异性糖基化和固相酶促寡糖合成中的应用。
7. Methods for Improving Enzymatic Trans-glycosylation for Synthesis of Human Milk Oligosaccharide Biomimetics [O] . Zeuner Birgitte, Jers Carsten, Mikkelsen Jørn Dalgaard, 2014

机译：改进酶促反式糖基化合成人乳寡糖仿生药的方法
8. Toxicological Review of cis-1,2-Dichloroethylene and trans-1,2-Dichloroethylene (CAS Nos. cis: 156-592-2: trans- 156-60-5: mixture: 540-59-0). In Support of Summary Information on the Integrated Risk Information System (IRIS) [R] . Glizia, A., Thompson, C., Berner, T., 2010

机译：顺式-1,2-二氯乙烯和反式-1,2-二氯乙烯的毒理学综述（Cas Nos.cis：156-592-2：trans-156-60-5：混合物：540-59-0）。支持综合风险信息系统（IRIs）的摘要信息

Low-Concentration 1,2-trans β-Selective Glycosylation Strategy and ItsApplications in Oligosaccharide Synthesis

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