Preparation of 9‐fluoro‐9‐deoxy‐N‐[2‐14C]acetylneuraminic acid

FEBS Letters

Brossmer, R.¹  Conradt, H.S.¹  Bünsch, A.¹ 

[1] Institut für Biochemie II der Universität Heidelberg, Im Neuenheimer Feld 328, D-6900 Heidelberg, FRG

关键词: 9-Fluoro-9-deoxy-N-acetylneuraminic acid;    Sugar activation;    Radioactive sugar analog;    Sialyltransferase;    Enzyme specificity;    Sialoglycoprotein;    Mes;    2-(N-morpholino)ethanesulfonic acid;    ManNAc;    N-acetylmannosamine;    TLC;    thin-layer chromatography;   

DOI  :  10.1016/0014-5793(84)81331-9

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

9-Fluoro-9-deoxy-N-[2-¹⁴C]acetylneuraminic acid has been prepared from 6-fluoro-6-deoxy-N-acetylmannosamine and [2-¹⁴C]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-[2-¹⁴C]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-α₁-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.

【 授权许可】

Unknown