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Synthesis of an Aminooxy Derivative of the GM3 Antigen and Its Application in Oxime Ligation.

ABSTRACT: The anomeric aminooxy GM3 trisaccharide cancer antigen (Neu5Ac?2,3Gal?1,4Glc?-ONH₂) has been chemically synthesized using a linear glycosylation approach. The key step involves a highly ?(2,3)-stereoselective sialylation to a galactose acceptor. The Neu5Ac?2,3Gal 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.

SUBMITTER: Kleski KA

PROVIDER: S-EPMC7606269 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Synthesis of an Aminooxy Derivative of the GM3 Antigen and Its Application in Oxime Ligation.

Kleski Kristopher A KA Shi Mengchao M Lohman Matthew M Hymel Gabrielle T GT Gattoji Vinod K VK Andreana Peter R PR

The Journal of organic chemistry 20200501 24

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 am ...[more]

PMID: 32320231

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