Synthesis of Sulfur-Containing Analogues of αGalNAc (Tn-Antigen) and βGal1,3αGalNAc (T-Antigen) |
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Authors: | Irmgard Wenzl Norbert Neuwirth Alexander G Hedenetz Christian Fiedler Hansjörg Streicher Frank M Unger Walther Schmid |
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Institution: | Institut für Organische Chemie, Universit?t Wien, A-1090 Wien, Austria, AT Fakult?t für Chemie, Universit?t Konstanz, D-78457 Konstanz, Germany, DE Zentrum für Ultrastrukturforschung, Universit?t für Bodenkultur, A-1180 Wien, Austria, AT
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Abstract: | Summary. A method for the preparation of thio-analogues of the T- and Tn-antigen was developed. Thus, starting from a known N-acetamido-glucoside
derivative, the epidithio analogue of the Tn-antigen was accessible in a four-step reaction sequence. The corresponding epidithio
analogue and the thioanhydro derivative of the T-antigen were synthesized starting from a disaccharide derivative. For the
preparation of the epidithio analogue the sulfur atoms were introduced via thiocyanates in a stepwise fashion, using mesylate as the leaving group at C-6 and triflate as the leaving group at C-4 in
the reducing carbohydrate moiety. The synthesis of the thioanhydro analogue was achieved by introducing a thiocyanate group
at C-6 into the glucose moiety, followed by subsequent displacement of a mesylate group at C-4 under inversion of configuration
utilizing sodium methoxide.
Received October 16, 2001. Accepted November 7, 2001 |
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Keywords: | , ,Carbohydrates, T-Antigen, Tn-Antigen, Thio analogues, Glycosides, |
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