Interaction ofN-acetyl-4-, 7-, 8- or 9-deoxyneuraminic acids andN-acetyl-4-, 7- or 8-mono-epi- and-7,8-di-epineuraminic acids withN-acetylneuraminate lyase |
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| Authors: | Roland Schauer Sabine Stoll Erich Zbiral Erwin Schreiner HanNelore H Brandstetter Andrea Vasella Franz Baumberger |
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| Institution: | (1) Biochemisches Institut, Christian-Albrechts-Universität, Olshausenstr. 40, D-2300 Kiel, Federal Republic of Germany;(2) Institut für Organische Chemie, Universität Wien, Währinger Str. 38, A-1090 Wien, Austria;(3) Organisch-Chemisches Institut, Universität Zürich, Winterthurerstr. 190, CH-8057 Zürich, Switzerland |
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| Abstract: | Various deoxy- and epi-derivatives ofN-acetylneuraminic acid were synthesized and tested for their substrate properties withN-acetylneuraminate lyase fromClostridium perfringens.N-Acetyl-9-deoxyneuraminic acid is a good substrate,N-acetylneuraminic acid derivatives with epimeric configuration at C-7, C-8 or both are cleaved slowly, whileN-acetyl-4-epi-,N-acetyl-4-deoxy-,N-acetyl-7-deoxy-andN-acetyl-8-deoxyneuraminic acid are resistant to enzyme action.N-Acetyl-4-deoxyneuraminic acid andN-acetyl-4-epineuraminic acid competitively inhibit the enzyme. These studies give further insight into a mechanism proposed for the reversible cleavage of sialic acids byN-acetylneuraminate lyase. |
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| Keywords: | N-acetylneuraminate lyase N-acetyl-deoxyneuraminic acids N-acetyl-epineuraminic acids sialic acids competitive inhibition |
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