{"title":"弧菌 Biotype 2 Serovar A O 抗原二糖的化学合成,其中含有罕见的 L-GalpNAmA","authors":"Shengyong Zhu, Jing Hu, Qingjun You, Guangzong Tian, Xiaopeng Zou, Chunjun Qin, Jian Yin","doi":"10.1055/a-2341-3462","DOIUrl":null,"url":null,"abstract":"Vibrio vulnificus can cause severe infections internally and externally. The mortality rate of V. vulnificus-associated gangrene and septicemia has increased due to antibiotic resistance and the absence of human vaccine. Bacterial carbohydrates have been widely used in the development of bacterial vaccines. Here, a rare L-GalpNAmA-containing disaccharide exists in V. vulnificus biotype 2 serovar A O-antigen was synthesized from D-glucose and L-galactose. An investigation on the influence of different linkers on the disaccharide synthetic efficiency indicated that the amine linker has more practicality. Two α-glycosidic linkages were constructed with good stereoselectivity by using nonparticipating C2 azido group and solvent effect. An orthogonal protection strategy allowed introductions of carboxyl and acetamidino (Am) groups at the disaccharide stage. The synthesis of the amine-linked disaccharide will provide a basis for the preparation of the trisaccharide repeating unit and longer fragments of V. vulnificus biotype 2 serovar A O-antigen, as well as other complex glycans.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chemical Synthesis of a Disaccharide from Vibrio vulnificus Biotype 2 Serovar A O-antigen Containing a Rare L-GalpNAmA\",\"authors\":\"Shengyong Zhu, Jing Hu, Qingjun You, Guangzong Tian, Xiaopeng Zou, Chunjun Qin, Jian Yin\",\"doi\":\"10.1055/a-2341-3462\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Vibrio vulnificus can cause severe infections internally and externally. The mortality rate of V. vulnificus-associated gangrene and septicemia has increased due to antibiotic resistance and the absence of human vaccine. Bacterial carbohydrates have been widely used in the development of bacterial vaccines. Here, a rare L-GalpNAmA-containing disaccharide exists in V. vulnificus biotype 2 serovar A O-antigen was synthesized from D-glucose and L-galactose. An investigation on the influence of different linkers on the disaccharide synthetic efficiency indicated that the amine linker has more practicality. Two α-glycosidic linkages were constructed with good stereoselectivity by using nonparticipating C2 azido group and solvent effect. An orthogonal protection strategy allowed introductions of carboxyl and acetamidino (Am) groups at the disaccharide stage. The synthesis of the amine-linked disaccharide will provide a basis for the preparation of the trisaccharide repeating unit and longer fragments of V. vulnificus biotype 2 serovar A O-antigen, as well as other complex glycans.\",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-06-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2341-3462\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2341-3462","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
摘要
弧菌可引起严重的体内和体外感染。由于抗生素耐药性和人类疫苗的缺乏,弧菌相关性坏疽和败血症的死亡率有所上升。细菌碳水化合物已被广泛用于细菌疫苗的开发。在此,研究人员用 D-葡萄糖和 L-半乳糖合成了一种存在于弧菌生物型 2 血清 A O 抗原中的罕见的含 L-GalpNAmA 的双糖。关于不同连接体对双糖合成效率影响的研究表明,胺连接体更实用。利用非参与的 C2 叠氮基团和溶剂效应,构建了两个具有良好立体选择性的 α-糖苷键。正交保护策略允许在二糖阶段引入羧基和乙酰氨基(Am)基团。氨基连接二糖的合成将为制备弧菌生物 2 型血清 A 血清 O 抗原的三糖重复单元和更长的片段以及其他复杂的聚糖奠定基础。
Chemical Synthesis of a Disaccharide from Vibrio vulnificus Biotype 2 Serovar A O-antigen Containing a Rare L-GalpNAmA
Vibrio vulnificus can cause severe infections internally and externally. The mortality rate of V. vulnificus-associated gangrene and septicemia has increased due to antibiotic resistance and the absence of human vaccine. Bacterial carbohydrates have been widely used in the development of bacterial vaccines. Here, a rare L-GalpNAmA-containing disaccharide exists in V. vulnificus biotype 2 serovar A O-antigen was synthesized from D-glucose and L-galactose. An investigation on the influence of different linkers on the disaccharide synthetic efficiency indicated that the amine linker has more practicality. Two α-glycosidic linkages were constructed with good stereoselectivity by using nonparticipating C2 azido group and solvent effect. An orthogonal protection strategy allowed introductions of carboxyl and acetamidino (Am) groups at the disaccharide stage. The synthesis of the amine-linked disaccharide will provide a basis for the preparation of the trisaccharide repeating unit and longer fragments of V. vulnificus biotype 2 serovar A O-antigen, as well as other complex glycans.