The anomeric aminooxy GM3 trisaccharide cancer antigen (Neu5Acα2,3Galβ1,4Glcβ-ONH2) 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.
The anomeric aminooxy GM3 trisacchariden class="Disease">cancer antigen (Neu5Acα2,3Galβ1,4Glcβ-ONH2) has been chemically synthesized using a linearglycosylation 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 polysaccharidePS A1 via an oxime link.
Authors: Jefferson Chan; Andrew R Lewis; Deepani Indurugalla; Melissa Schur; Warren Wakarchuk; Andrew J Bennet Journal: J Am Chem Soc Date: 2012-02-17 Impact factor: 15.419
Authors: Mengchao Shi; Kristopher A Kleski; Kevin R Trabbic; Jean-Paul Bourgault; Peter R Andreana Journal: J Am Chem Soc Date: 2016-10-21 Impact factor: 15.419
Authors: Martin A Cheever; James P Allison; Andrea S Ferris; Olivera J Finn; Benjamin M Hastings; Toby T Hecht; Ira Mellman; Sheila A Prindiville; Jaye L Viner; Louis M Weiner; Lynn M Matrisian Journal: Clin Cancer Res Date: 2009-09-01 Impact factor: 12.531