Facile Synthesis of Saponins Containing 2,3-Branched Oligosaccharides by Using Partially Protected Glycosyl Donors

Authors
Gu, Guofeng
Du, Yuguo
Linhardt, Robert J.
ORCID
https://orcid.org/0000-0003-2219-5833
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Issue Date
2004-08-06
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Full Citation
Facile Synthesis of Saponins Containing 2,3-Branched Oligosaccharides by Using Partially Protected Glycosyl Donors, G. Gu, Y. Du, R. J. Linhardt, Journal of Organic Chemistry, 69, 5497-5500, 2004.
Abstract
Two natural saponins 1 and 2, isolated from Solanum indicum L., and containing 2,3-branched sugar moieties, have been efficiently synthesized. Partially protected monosaccharide and disaccharide donors were used to facilitate target synthesis. Stereo factors were critical in incorporating 2,3-branched sugars on steroid aglycones. Saponin 1 was synthesized in five steps and 30% overall yield, while saponin 2 was obtained using six straightforward sequential reactions in 31% overall yield. Saponin 2 shows promising cytotoxic activity toward human hepatocellular carcinoma BEL-7402 with an IC50 of <6 μg/mL.
Description
Journal of Organic Chemistry, 69, 5497-5500
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Department
The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
Publisher
American Chemical Society (ACS)
Relationships
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Journal of Organic Chemistry
https://harc.rpi.edu/
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A full text version is available in DSpace@RPI