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.
Similar content being viewed by others
References
Corfield AP, Schauer R (1982) in Sialic Acids, Cell Biol Monogr 10, ed. Schauer R, Springer, Wien, p 195–261.
Schauer R (1982) Adv Carbohydr Chem Biochem 40:131–234.
DeVries GH, Binkley SB (1972) Arch Biochem Biophys 151:234–42.
Nees S, Schauer R, Mayer F, Ehrlich K (1976) Hoppe Seylers Z Physiol Chem 357:839–53.
Kawakami B, Kudo T, Narahashi Y, Horikoshi K (1986) Agric Biol Chem 50:2155–58.
Uchida Y, Tsukada Y, Sugimori T (1984) J Biochem (Tokyo) 96:507–22.
Brunetti P, Jourdian GW, Roseman S (1962) J Biol Chem 237:2447–53.
Warren L (1986) Biochim Biophys Acta 888:278–81.
Aisaka K, Uwajima T (1986) Appl Environ Microbiol 51:562–65.
Schauer R, Wember M (1971) Hoppe Seylers Z Physiol Chem 352:1517–23.
Schauer R, Wember M, Wirtz-Peitz F, Ferreira do Amaral C (1971) Hoppe Seylers Z Physiol Chem 352:1073–80.
Shukla AK, Schauer R (1986) Anal Biochem 158:158–64.
Beau J-M, Schauer R (1980) Eur J Biochem 106:531–40.
Suttajit M, Winzler R (1971) J Biol Chem 246:3398–404.
Suttajit M, Urban C, McLean RL (1971) J Biol Chem 246:810–14.
Baumberger F, Vasella A (1986) Helv Chim Acta 69:1535–41.
Zbiral E, Schreiner E, Brandstetter HH (1987) Monatsh Chem, in press.
Baumberger F, Vasella A (1986) Helv Chim Acta 69:1205–15.
Villalva Basabe J, Brossmer R (1984) Abstr 12th Int Carbohydr Symp, eds. Vliegenthart JFG, Kamerling JP, Veldink GA, Vonk, Utrecht, p 21 and 223.
Zbiral E, Brandstetter HH (1985) Monatsh Chem 116:87–98.
Comb DG, Roseman S (1960) J Biol Chem 235:2529–37.
Schauer R (1978) Methods Enzymol 50:64–89.
Dixon M, Webb EC, eds. (1979) in Enzymes, 3rd edn., Longman, London, p 348.
Zbiral E, Brandstetter HH, Christian R, Schauer R (1987) Liebigs Ann Chem, in press.
Conradt HS, Bünsch A, Brossmer R (1984) FEBS Letters 170:295–300.
Brossmer R, Rose U, Kasper D, Smith TL, Grasmuk H, Unger FM (1980) Biochem Biophys Res Commun 96:1282–89.
Hagedorn H, Mack H, Gross HJ, Brossmer R (1986) Abstr 13th Int Carbohydr Symp, Ithaca, p 13.
Gantt R, Millner S, Binkley SB (1964) Biochemistry 3:1952–60.
DeVries GH, Binkley SB (1972) Arch Biochem Biophys 151:243–50.
Villalva Basabe J, Gross HJ, Brossmer R (1985) Abstr 3rd Eur Symp Carbohydr, ed. Defaye J, Imprim Bibl Interuniv, Grenoble, p 140.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Schauer, R., Stoll, S., Zbiral, E. et al. 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. Glycoconjugate J 4, 361–369 (1987). https://doi.org/10.1007/BF01048369
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01048369