Streamlined Synthesis and Evaluation of Teichoic Acid Fragments.
Daan van der Es, Francesca Berni, Wouter F J Hogendorf, Nico Meeuwenoord, Diana Laverde, Angela van Diepen, Herman S Overkleeft, Dmitri V Filippov, Cornelis H Hokke, Johannes Huebner, Gijsbert A van der Marel, Jeroen D C Codée
Author Information
Daan van der Es: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands. ORCID
Francesca Berni: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands.
Wouter F J Hogendorf: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands.
Nico Meeuwenoord: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands.
Diana Laverde: Division of Paediatric Infectious Diseases, Dr. von Hauner Children's Hospital, Ludwig-Maximilians-University, Munich, Germany.
Angela van Diepen: Department of Parasitology, Leiden University Medical Center, Albinusdreef 2, 2333 ZA, Leiden, The Netherlands.
Herman S Overkleeft: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands.
Dmitri V Filippov: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands.
Cornelis H Hokke: Department of Parasitology, Leiden University Medical Center, Albinusdreef 2, 2333 ZA, Leiden, The Netherlands.
Johannes Huebner: Division of Paediatric Infectious Diseases, Dr. von Hauner Children's Hospital, Ludwig-Maximilians-University, Munich, Germany.
Gijsbert A van der Marel: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands.
Jeroen D C Codée: Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333, CC, Leiden, The Netherlands. ORCID
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.
