Highly Efficient Syntheses of Hyaluronic Acid Oligosaccharides
- 19 December 2006
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 13 (2) , 529-540
- https://doi.org/10.1002/chem.200601090
Abstract
Highly efficient syntheses of hyaluronic acid oligosaccharides have been accomplished through the pre‐activation based iterative one‐pot strategy. A series of oligosaccharides ranging from di‐ to hexasaccharides were rapidly assembled using only near stoichiometric amounts of the building blocks without aglycon adjustment or purifications of intermediate oligosaccharides. Deprotection and oxidation protocols were developed for protective group removal and oxidation‐state adjustment. The availability of such structurally well defined synthetic hyaluronic acid oligosaccharides will greatly facilitate the establishment of detailed structure–function relationships.Keywords
This publication has 59 references indexed in Scilit:
- A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids and Its Application in Glycosaminoglycan SynthesesChemistry – A European Journal, 2006
- Chemical approaches to deciphering the glycosaminoglycan codeCurrent Opinion in Chemical Biology, 2005
- An Expedient Synthesis of the Repeating Unit of the Acidic Polysaccharide of the Bacteriolytic Complex of LysoamidaseChemistry – A European Journal, 2004
- Iterative One‐Pot Synthesis of OligosaccharidesAngewandte Chemie International Edition in English, 2004
- Iterative One-Pot Synthesis of OligosaccharidesAngewandte Chemie, 2004
- Ein synthetisches Antithrombin III bindendes Pentasaccharid ist jetzt ein Wirkstoff! Was kommt danach?Angewandte Chemie, 2004
- Synthesis of Heparin OligosaccharidesJournal of the American Chemical Society, 2003
- Oligosaccharides of Hyaluronan Activate Dendritic Cells via Toll-like Receptor 4The Journal of Experimental Medicine, 2002
- Programmable One-Pot Oligosaccharide SynthesisJournal of the American Chemical Society, 1999
- Solvent and Other Effects on the Stereoselectivity of Thioglycoside GlycosidationsSynlett, 1997