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Preparation of 9‐fluoro‐9‐deoxy‐ N ‐[2‐ 14 C]acetylneuraminic acid
Author(s) -
Conradt H.S.,
Bünsch A.,
Brossmer R.
Publication year - 1984
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(84)81331-9
Subject(s) - sialyltransferase , chemistry , sialidase , n acetylneuraminic acid , pyruvic acid , neuraminic acid , yield (engineering) , biochemistry , clostridium perfringens , enzyme , sialic acid , vibrio cholerae , lyase , stereochemistry , neuraminidase , bacteria , biology , materials science , metallurgy , genetics
9‐Fluoro‐9‐deoxy‐ N ‐[2‐ 14 C]acetylneuraminic acid has been prepared from 6‐fluoro‐6‐deoxy‐ N ‐acetylmannosamine and [2‐ 14 C]pyruvic acid for the first time, using Clostridium perfringens N ‐acetylneuraminate pyruvate‐lyase (EC 4.1.3.3). The fluoro sugar was activated by CMP‐ N ‐acetylneuraminic acid synthase and CTP to yield CMP‐9‐fluoro‐9‐deoxy‐ N ‐[2‐ 14 C]acetylneuraminic acid. Both products were obtained in good yield (60 and 30%, respectively). The radioactive sugar in its activated form is glycosidically attached to asialo‐α 1 ‐acid glycoprotein by sialyltransferase and can be removed by the action of Vibrio cholerae sialidase. The reaction rates of the enzymes studied are lower with the 9‐fluoro derivatives than with the N ‐acetylneuraminic acid substrates.