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Development of Novel Glycosyl Donors for 1,2‐cis Glycosylation Reaction for Amino Sugar and Synthesis of anti‐Helicobacter pylori Oligosaccharide
| Content Provider | Semantic Scholar |
|---|---|
| Author | Manabe, Shino Ishii, Kazuyuki Ito, Yukishige |
| Copyright Year | 2009 |
| Abstract | Despite advances in synthetic carbohydrate chemistry, the 1,2-cis-selective glycosylation reaction of 2-deoxy2-amino sugars has not progressed during the last three decades. For such glycosylations, 2-azide glycosyl donors have been extensively employed, notwithstanding di‹culties in their preparation and moderate selectivities. Herein, we report on a highly 1,2-cis-selective trans-carbamate sugar donor, which can be readily prepared in high yields. Furthermore, the utility of the novel cis-selective glycosyl donor for preparing complex oligosaccharides is demonstrated through the eŠective synthesis of an antiHelicobacter pylori hexasaccharide. A. Introduction Bioactive oligosaccharides from natural resources typically include 1,2-cis glycosides of amino sugars, such as glycosylphosphatidylinositol (GPI) anchor 1, aminoglycoside antibiotics 2, and glycosaminoglycan oligosaccharides 3 (Fig. 1) (1). Biological studies of such saccharides, however, will rely on organic synthetic chemistry to provide satisfactory amounts of the oligosaccharides with various structures, including non-natural structures. Furthermore, organic synthesis can provide glycoconjugates that are photoa‹nity or ‰uorescent labeled for biological research. Although synthetic carbohydrate chemistry has developed signiˆcantly over the last two decades, preparation of 1,2-cis amino sugars has remained unchanged (2). The current method for 1,2-cis selective glycosylation for amino sugars, which was developed by two prominent sugar chemists, Lemieux and Paulsen, over 30 years ago (3,4), involves glycosyl 2-azido donor 4, and remains as |
| Starting Page | 187 |
| Ending Page | 202 |
| Page Count | 16 |
| File Format | PDF HTM / HTML |
| DOI | 10.1002/chin.200939269 |
| Volume Number | 40 |
| Alternate Webpage(s) | https://www.jstage.jst.go.jp/article/tigg/20/114/20_114_187/_pdf |
| Alternate Webpage(s) | https://doi.org/10.1002/chin.200939269 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
