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A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE)
Open accessAbstract
A new solid phase method for the synthesis of complex oligosaccharides is described. The method involves attachment to phenolic polystyrene of the first carbohydrate unit, through its anomeric position and via a photolabile linker, using dimethylthiomethylsulfonium triflate as an activator. Reiteration of the glycosidation process allows stereocontrolled growth of linear or branched oligosaccharides in high yield. Cleavage from the resin is efficiently achieved photolytically. The application of the method to the total prepn. of the heptasaccharide phytoalexin elicitor (HPE) is described.
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Cites
Sharp, J. K., Valent, B., & Albersheim, P. (1984) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)90864-1 · Cited by 295
Cited by
New Principles for Glycoside‐Bond Formation
Zhu, X., & Schmidt, R. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200802036 · Cited by 957
Automated Solid-Phase Synthesis of Oligosaccharides
Plante, O. J., Palmacci, E. R., & Seeberger, P. H. (2001) · Science · doi:10.1126/science.1057324 · Cited by 933
Linkers and Cleavage Strategies in Solid-Phase Organic Synthesis and Combinatorial Chemistry
Guillier, F., Orain, D., & Bradley, M. (2000) · Chemical Reviews · doi:10.1021/cr980040+ · Cited by 516
Metadata
- Authors
- Nicolaou, K. C., Winssinger, N., Pastor, J., & DeRoose, F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-01-01
- Volume
- 119
- Issue
- 2
- Pages
- 449-450
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2019141135
- Cited by
- 229
- References
- 1
- FWCI
- 21.34
- Type
- journal article
- Language
- en
- Open access
- green
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- Nicolaou, K. C., Winssinger, N., Pastor, J., & DeRoose, F. (1997). A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE). Journal of the American Chemical Society. https://doi.org/10.1021/ja963482g
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
