Bulletin of the Korean Chemical Society

  • 제29권7호
  • /
  • Pages.1315-1319
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  • 2008
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of the 2'-Azidoethyl Trisaccharide, 6d-altroHepp-GlcNAc-Gal Hapten, an O-Antigenic Repeating Unit of Campylobacter jejuni Serotypes O:23 and O:36

  • Yun, Mi-Kyung (Department of Applied Chemistry, Dongyang Technical College) ;
  • Shin, Jeong E. Nam (Department of Chemistry, Soongsil University)
  • 발행 : 2008.07.20
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초록

A trisaccharide, 6d-Altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$3) Gal$\alpha$ (1$\rightarrow$$OCH_2CH_2N_3$, as an O-antigenic repeating unit of Campylobacter jejuni serotypes O:23 and O:36, was synthesized. Coupling of the 6d-altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$SEt donor with Gal$\alpha$ (1${\rightarrow}OCH_2CH_2Cl$ acceptor in the presence of NIS-TfOH promoter afforded the trisaccharide having the $\beta$ (1$\rightarrow$3) Gal linkage. $\beta$ -Stereospecificity and the desired regioselectivity for the 3-OH Gal are obtained. Subsequent hydrogenation, acetylation, azide displacement, hydrazinolysis, Nacetylation, and finally deacetylation furnished the title trisaccharide hapten for further glycoconjugation.

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참고문헌

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  3. Progress toward the Development of Glycan-Based Vaccines against Campylobacteriosis vol.7, pp.5, 2008, https://doi.org/10.1021/acsinfecdis.0c00332