Anomeric Reactivity-Based One-Pot Synthesis of Heparin-Like Oligosaccharides
- 1 October 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (42) , 12795-12800
- https://doi.org/10.1021/ja073098r
Abstract
A highly efficient one-pot methodology is described for the synthesis of heparin and heparan sulfate oligosaccharides utilizing thioglycosides with well-defined reactivity as building blocks. l-Idopyranosyl and d-glucopyranosyl thioglycosides 5 and 10 were used as donors due to low reactivity of uronic acids as the glycosyl donors in the one-pot synthesis. The formation of uronic acids by a selective oxidation at C-6 was performed after assembly of the oligosaccharides. The efficiency of this programmable strategy with the flexibility for sulfate incorporation was demonstrated in the representative synthesis of disaccharides 17, 18, tetrasaccharide 23, and pentasaccharide 26.Keywords
This publication has 34 references indexed in Scilit:
- Programmable reactivity-based one-pot oligosaccharide synthesisNature Protocols, 2006
- Microarrays of Synthetic Heparin OligosaccharidesJournal of the American Chemical Society, 2006
- A Modular Strategy Toward the Synthesis of Heparin-like Oligosaccharides Using Monomeric Building Blocks in a Sequential Glycosylation StrategyJournal of the American Chemical Society, 2005
- Synthesis of Heparin OligosaccharidesJournal of the American Chemical Society, 2003
- Chemical Contributions to Understanding Heparin Activity: Synthesis of Related Sulfated OligosaccharidesEuropean Journal of Organic Chemistry, 2003
- Synthesis of threeSalmonellaepitopes for biosensor studies of carbohydrate–antibody interactionsCanadian Journal of Chemistry, 2002
- Synthesis of a Versatile Neuraminic Acid “C”-Disaccharide Precursor for the Synthesis ofC-Glycoside Analogues of GangliosidesThe Journal of Organic Chemistry, 1999
- Programmable One-Pot Oligosaccharide SynthesisJournal of the American Chemical Society, 1999
- A Convergent Synthesis of a Hexadecasaccharide Fragment of the O-Polysaccharide of Shigella dysenteriae Type 1Journal of the American Chemical Society, 1995
- PROTEOGLYCANS: STRUCTURES AND INTERACTIONSAnnual Review of Biochemistry, 1991