Light fluorous synthesis of glucosylated glycerol teichoic acids

W F J Hogendorf; A Kropec; D V Filippov; H S Overkleeft; J Huebner; G A van der Marel; J D C Codée

doi:10.1016/j.carres.2012.02.023

Light fluorous synthesis of glucosylated glycerol teichoic acids

Carbohydr Res. 2012 Jul 15:356:142-51. doi: 10.1016/j.carres.2012.02.023. Epub 2012 Mar 6.

Authors

W F J Hogendorf¹, A Kropec, D V Filippov, H S Overkleeft, J Huebner, G A van der Marel, J D C Codée

Affiliation

¹ Leiden Institute of Chemistry, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 22429772
DOI: 10.1016/j.carres.2012.02.023

Abstract

We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl)glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel α-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol.

MeSH terms

Cell Wall / chemistry
Enterococcus faecalis / chemistry*
Glycosylation
Hydrocarbons, Fluorinated / chemistry*
Molecular Structure
Organophosphorus Compounds / chemistry
Teichoic Acids / chemical synthesis*

Substances

Hydrocarbons, Fluorinated
Organophosphorus Compounds
Teichoic Acids