TY - JOUR
T1 - Synthesis of a Pentasaccharide Repeating Unit of Lipopolysaccharide Derived from Virulent E. coli O1 and Identification of a Glycotope Candidate of Avian Pathogenic E. coli O1
AU - Nishi, Nobuya
AU - Seki, Katsunori
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
N1 - Funding Information:
We wish to thank Mr. Daisuke Yoshidome (Schrödinger K.K.) for helpful advices about the DFT calculations. This research was supported in part by a JSPS KAKENHI Grant Numbers JP20K21289 in Challenging Research (Exploratory), JP19H02724 in Scientific Research (B), JP19J13223 in JSPS Fellows, and the Sasagawa Scientific Research Grant from the Japan Science Society.
Publisher Copyright:
© 2020 Wiley-VCH GmbH
PY - 2021/1/25
Y1 - 2021/1/25
N2 - Avian pathogenic Escherichia coli (APEC) is a common bacterial pathogen infecting chickens, resulting in economic losses to the poultry industry worldwide. In particular, APEC O1, one of the most common serotypes of APEC, is considered problematic due to its zoonotic potential. Therefore, many attempts have been made to develop an effective vaccine against APEC O1. In fact, the lipopolysaccharide (LPS) O-antigen of APEC O1 has been shown to be a potent antigen for inducing specific protective immune responses. However, the detailed structure of the O-antigen of APEC O1 is not clear. The present study demonstrates the first synthesis of a pentasaccharide repeating unit of LPS derived from virulent E. coli O1 and its conjugate with BSA. ELISA tests using the semi-synthetic glycoconjugate and the APEC O1 immune chicken serum revealed that the pentasaccharide is a glycotope candidate of APEC O1, with great potential as an antigen for vaccine development.
AB - Avian pathogenic Escherichia coli (APEC) is a common bacterial pathogen infecting chickens, resulting in economic losses to the poultry industry worldwide. In particular, APEC O1, one of the most common serotypes of APEC, is considered problematic due to its zoonotic potential. Therefore, many attempts have been made to develop an effective vaccine against APEC O1. In fact, the lipopolysaccharide (LPS) O-antigen of APEC O1 has been shown to be a potent antigen for inducing specific protective immune responses. However, the detailed structure of the O-antigen of APEC O1 is not clear. The present study demonstrates the first synthesis of a pentasaccharide repeating unit of LPS derived from virulent E. coli O1 and its conjugate with BSA. ELISA tests using the semi-synthetic glycoconjugate and the APEC O1 immune chicken serum revealed that the pentasaccharide is a glycotope candidate of APEC O1, with great potential as an antigen for vaccine development.
KW - avian pathogenic Escherichia coli
KW - boron-mediated aglycon delivery
KW - glycoconjugate
KW - glycotope
KW - β-rhamnoside
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U2 - 10.1002/anie.202013729
DO - 10.1002/anie.202013729
M3 - Article
C2 - 33124093
AN - SCOPUS:85097814545
SN - 1433-7851
VL - 60
SP - 1789
EP - 1796
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 4
ER -