title: Light fluorous synthesis of glucosylated glycerol teichoic acids.
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.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: W F J
authors.initials: WF
authors.lastname: Hogendorf
authors.forename: A
authors.initials: A
authors.lastname: Kropec
authors.forename: D V
authors.initials: DV
authors.lastname: Filippov
authors.forename: H S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: J
authors.initials: J
authors.lastname: Huebner
authors.forename: G A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: J D C
authors.initials: JD
authors.lastname: Codée
mesh_terms: D002473:Cell Wall / Q000737:chemistry; D013293:Enterococcus faecalis / Q000737:chemistry*; D006031:Glycosylation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry; D013682:Teichoic Acids / Q000138:chemical synthesis*
chemical_list: D006845:Hydrocarbons, Fluorinated; D009943:Organophosphorus Compounds; D013682:Teichoic Acids