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Mechanism of human alpha-1,3-fucosyltransferase V : glycosidic cleavage occurs prior to nucleophilic attack

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1997

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Murray, Brion W.
Burkart, Michael D.
Hung, Shang-Cheng
Wong, Chi-Huey

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Biochemistry. 1997, 36(4), pp. 823-831. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi962284z

Zusammenfassung

α-1,3-Fucosyltransferase V (FucT V) catalyzes the transfer of l-fucose from the donor sugar guanosine 5'-diphospho-β-l-fucose (GDP-Fuc) to an acceptor sugar. A secondary isotope effect on the fucosyltransfer reaction with guanosine 5'-diphospho-[1-²H]-β-l-fucose (GDP-[1-²H]-Fuc) as the substrate was observed and determined to be DV = 1.32 + 0.13 and DV/K = 1.27 + 0.07. Competitive inhibition of FucT V by guanosine 5'-diphospho-2-deoxy-2-fluoro-β-l-fucose (GDP-2F-Fuc) was observed with an inhibition constant of 4.2 íM which represents the most potent inhibitor of this enzyme to date. Incubation of GDP-2F-Fuc with FucT V and an acceptor molecule prior to the addition of GDP-Fuc had no effect on the potency of inhibition, indicating that GDP-2F-Fuc is neither an inactivator nor a slow substrate. Both the observed secondary isotope effect and the inhibition by GDP-2F-Fuc are consistent with a charged, sp²-hybridized, transition-state structure. A convenient and efficient synthesis of GDP-[1-²H]-Fuc and GDP-2F-Fuc and a nonradioactive, fluorescence assay for fucosyltransferase activity have been developed.

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540 Chemie

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ISO 690MURRAY, Brion W., Valentin WITTMANN, Michael D. BURKART, Shang-Cheng HUNG, Chi-Huey WONG, 1997. Mechanism of human alpha-1,3-fucosyltransferase V : glycosidic cleavage occurs prior to nucleophilic attack. In: Biochemistry. 1997, 36(4), pp. 823-831. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi962284z
BibTex
@article{Murray1997Mecha-9726,
  year={1997},
  doi={10.1021/bi962284z},
  title={Mechanism of human alpha-1,3-fucosyltransferase V : glycosidic cleavage occurs prior to nucleophilic attack},
  number={4},
  volume={36},
  issn={0006-2960},
  journal={Biochemistry},
  pages={823--831},
  author={Murray, Brion W. and Wittmann, Valentin and Burkart, Michael D. and Hung, Shang-Cheng and Wong, Chi-Huey}
}
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