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Es, Daan van der; Berni, Francesca; Hogendorf, Wouter F. J.; Meeuwenoord, Nico; Laverde, Diana; Diepen, Angela van; Overkleeft, Herman S.; Filippov, Dmitri V.; Hokke, Cornelis H.; Hübner, Johannes; Marel, Gijsbert A. van der; Codee, Jeroen D. C. (2018): Streamlined Synthesis and Evaluation of Teichoic Acid Fragments. In: Chemistry-A European Journal, Vol. 24, No. 16: pp. 4014-4018
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Teichoic acids (TAs) are key components of the Gram-positive bacterial cell wall that are composed of alditol phosphate repeating units, decorated with alanine or carbohydrate appendages. Because of their microhetereogeneity, pure well-defined TAs for biological or immunological evaluation cannot be obtained from natural sources. We present here a streamlined automated solid-phase synthesis approach for the rapid generation of well-defined glycosylated, glycerol-based TA oligomers. Building on the use of a universal linker system and fluorous tag purification strategy, a library of glycerolphosphate pentadecamers, decorated with various carbohydrate appendages, is generated. These are used to create a structurally diverse TA-microarray, which is used to reveal, for the first time, the binding preferences of anti-LTA (lipoteichoic acids) antibodies at the molecular level.