期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 10, 页码 5193-5198出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202015141
关键词
all-nitrogenated sugar; aminoglycosides; domino reaction; iminosugar; sigmatropic rearrangement
资金
- MEXT [19K22189, 18K06137]
- Mizutani Foundation for Glycoscience
- JSPS [19J12788]
- Grants-in-Aid for Scientific Research [19K22189, 19J12788, 18K06137] Funding Source: KAKEN
A concise synthetic route to peracetylated all-nitrogenated sugars (ANSs) in seven steps from commercially available monosaccharides has been developed. The key to success is the use of sequential Overman rearrangement for ANS synthesis, which shows cytotoxicity against human cancer cell lines.
All-nitrogenated sugars (ANSs), in which all hydroxy groups in a carbohydrate are replaced with amino groups, are anticipated to be privileged structures with useful biological activities. However, ANS synthesis has been challenging due to the difficulty in the installation of multi-amino groups. We report herein the development of a concise synthetic route to peracetylated ANSs in seven steps from commercially available monosaccharides. The key to success is the use of the sequential Overman rearrangement, which enables formal simultaneous substitution of four or five hydroxy groups in monosaccharides with amino groups. A variety of ANSs are available through the same reaction sequence starting from different initial monosaccharides by chirality transfer of secondary alcohols. Transformations of the resulting peracetylated ANSs such as glycosylation and deacetylation are also demonstrated. Biological studies reveal that ANS-modified cholesterol show cytotoxicity against human cancer cell lines, whereas each ANS and cholesterol have no cytotoxicity.
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