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http://dx.doi.org/10.5012/bkcs.2008.29.7.1315

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)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.7, 2008 , pp. 1315-1319 More about this Journal
Abstract
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.
Keywords
Campylobacter jejuni; Trisaccharide; 6d-altroHepp-GlcNAc-Gal hapten; O-Antigenic repeating unit
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