| Autor: |
Kleski KA; Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States., Shi M; Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States., Lohman M; Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States., Hymel GT; Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States., Gattoji VK; Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States., Andreana PR; Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States. |
| Abstrakt: |
The anomeric aminooxy GM3 trisaccharide cancer antigen (Neu5Acα2,3Galβ1,4Glcβ-ONH 2 ) has been chemically synthesized using a linear glycosylation approach. The key step involves a highly α(2,3)-stereoselective sialylation to a galactose acceptor. The Neu5Acα2,3Gal intermediate was functionalized as a donor for a [2 + 1] glycosylation, including a glucose acceptor that featured an O -succinimidyl group on the reducing end as an aminooxy precursor. The fully deprotected anomeric aminooxy GM3 trisaccharide was then conjugated to the immunologically relevant zwitterionic polysaccharide PS A1 via an oxime link. |
