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O43 四糖重复单元的全合成。

Total Synthesis of O43 Tetrasaccharide Repeating Unit.

机构信息

Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

出版信息

J Org Chem. 2024 Mar 15;89(6):4019-4030. doi: 10.1021/acs.joc.3c02886. Epub 2024 Feb 25.

Abstract

is a pathogen responsible for the deadly pandemic - cholera. The glycans present on the surface of various strains of are considered as potential vaccine candidates. The tetrasaccharide repeating unit (RU) of O43 is decorated with less-explored rare deoxy amino sugars like d-quinosamine and d-viosamine, along with a rare amino acid, -acetyl-l-allothreonine. Herein, we report a detailed account of the total synthesis of O43 tetrasaccharide RU. In our earlier attempt, while a one-pot assembly of trisaccharide was successful, the final coupling with a fully functionalized d-viosamine donor was low yielding. The successful route involved employing the Fmoc-protected d-viosamine building block as a donor and a late-stage amide bond formation of the tetrasaccharide.

摘要

是一种引起致命性大流行疾病——霍乱的病原体。各种 菌株表面的聚糖被认为是潜在的疫苗候选物。O43 的四糖重复单元 (RU) 带有较少探索的稀有去氧氨基糖,如 d-喹诺胺和 d-粘霉胺,以及一种稀有氨基酸,-乙酰-l-allo 苏氨酸。在此,我们报告了 O43 四糖 RU 的全合成的详细说明。在我们之前的尝试中,虽然一锅法组装三糖是成功的,但与完全功能化的 d-粘霉胺供体的最后偶联产率较低。成功的路线涉及使用 Fmoc 保护的 d-粘霉胺砌块作为供体和四糖的后期酰胺键形成。

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