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Light fluorous synthesis of glucosylated glycerol teichoic acids.

Carbohydr. Res.. 2019-07; 
HogendorfW F J,KropecA,FilippovD V,OverkleeftH S,HuebnerJ,van der MarelG A,CodéeJ
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Gene Synthesis … Scheme 2. Synthesis of phosphoramidite 18 and perfluorooctylpropyl succinyl linked glycosyl glycerol 20 … All chemicals (Acros, Fluka, Merck, Schleicher & Schuell, Sigma–Aldrich, Genscript) were used as received and reactions were carried out dry, under an argon atmosphere … Get A Quote

摘要

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 f... More

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