2024-03-28T14:24:29Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/990442018-05-18T09:18:45Zcom_10261_38com_10261_5col_10261_291
2014-06-27T06:34:44Z
urn:hdl:10261/99044
Synthesis of Chondroitin Sulfate Oligosaccharides Using N-(Tetrachlorophthaloyl)- and N-(Trifluoroacetyl)galactosamine Building Blocks
Macchione, Giuseppe
Maza, Susana
Kayser, M. Mar
de Paz, José L.
Nieto, Pedro M.
Carbohydrates
Oligosaccharides
Glycosylation
Glycosaminoglycans
Protecting groups
We have explored synthetic routes for the preparation of chondroitin sulfate (CS) oligosaccharides based on the use of N-tetrachlorophthaloyl- (N-TCP) and N-trifluoroacetyl-substituted (N-TFA) galactosamine building blocks. Using N-TCP units, we carried out the total synthesis of two CS disaccharides, demonstrating the compatibility of TCP protection with the final deprotection/sulfation steps. However, an attempted 2 + 2 coupling of N-TCP-containing disaccharides for the synthesis of CS tetrasaccharides failed. In contrast, a synthetic route using N-TFA galactosamine units efficiently led to biologically relevant CS-like oligosaccharides. The N-TFA groups could easily be removed at the end of the synthesis, and microwave irradiation greatly facilitated the sulfation reactions. The utility of this approach is illustrated with the total synthesis of two CS-like tetrasaccharides with different sulfate distribution patterns. Finally, we used a fluorescence polarization assay to estimate the relative abilities of the synthesized compounds to inhibit the interaction between FGF-2 and heparin.
2014-06-27T06:34:44Z
2014-06-27T06:34:44Z
2014
artículo
European Journal of Organic Chemistry, 18: 3868-3884 (2014)
http://hdl.handle.net/10261/99044
10.1002/ejoc.201402222
eng
Postprint
http://dx.doi.org/10.1002/ejoc.201402222
Sí
openAccess
Wiley-Blackwell