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- Title
Streamlined Synthesis and Evaluation of Teichoic Acid Fragments.
- Authors
van der Es, Daan; Berni, Francesca; Hogendorf, Wouter F. J.; Meeuwenoord, Nico; Laverde, Diana; van Diepen, Angela; Overkleeft, Herman S.; Filippov, Dmitri V.; Hokke, Cornelis H.; Huebner, Johannes; van der Marel, Gijsbert A.; Codée, Jeroen D. C.
- Abstract
Abstract: 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.
- Subjects
TEICHOIC acid; GRAM-positive bacteria; GLYCEROLPHOSPHATE dehydrogenase; ALANINE; LIPOTEICHOIC acid
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 16, p4014
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201800153