Sialylations reactions: Expanding the effect of silicon protecting groups at C-4

Alexanndra Behm; Jessica Hafner; Natalie Goeckner; Matthew Lohman; Cristina De Meo

doi:10.1016/j.carres.2022.108707

Sialylations reactions: Expanding the effect of silicon protecting groups at C-4

Carbohydr Res. 2022 Dec:522:108707. doi: 10.1016/j.carres.2022.108707. Epub 2022 Oct 18.

Authors

Alexanndra Behm¹, Jessica Hafner¹, Natalie Goeckner¹, Matthew Lohman¹, Cristina De Meo²

Affiliations

¹ Chemistry Department at Southern Illinois University Edwardsville, Edwardsville, IL, 62026, USA.
² Chemistry Department at Southern Illinois University Edwardsville, Edwardsville, IL, 62026, USA. Electronic address: cdemeo@siue.edu.

PMID: 36279591
DOI: 10.1016/j.carres.2022.108707

Abstract

As a part of a general research goal into evaluating the effect of O-protecting groups in sialylation reactions, we compared the reactivities of phenylthio α- and β-sialyl donors protected at C-4 with tert-butyldimethyl silyl (TBDMS) and tri-isopropylsilyl (TIPS) groups in the coupling with primary and secondary galactosyl acceptors. The effect of the solvent and the donor's anomeric configuration were investigated and compared to previously published data. It is demonstrated that silicon groups at C-4 have a significant influence on sialylation reactions, and in general their overall performance is optimized with the use of acetonitrile.

Keywords: O-glycosylation; Sialic acid; Silyl protecting groups.

MeSH terms

Glycosylation
Silicon*
Solvents
Stereoisomerism

Substances

Silicon
Solvents