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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 7
BKCSDE 29(7)
July 20, 2008 

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
Mikyung Yun, Jeong E. Nam Shin*
Campylobacter jejuni, Trisaccharide, 6d-altroHepp-GlcNAc-Gal hapten, O-Antigenic repeating unit
A trisaccharide, 6d-Altro-Hep (1→3) GlcNAcβ (1→3) Galα (1→OCH2CH2N3, as an O-antigenic repeating unit of Campylobacter jejuni serotypes O:23 and O:36, was synthesized. Coupling of the 6d-altro-Heppα (1→3) GlcNAcβ (1→SEt donor with Galα (1→OCH2CH2Cl acceptor in the presence of NIS-TfOH promoter afforded the trisaccharide having the β(1→3) Gal linkage. β-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.
1315 - 1319
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