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Inhibition of dextransucrase by α-D-Glucose derivatives

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Abstract

α-D-Glucopyranosyl fluoride was modified at positions 2, 3, or 5 and these analogs were tested as substrates and inhibitors of dextransucrase fromLeuconostoc mesenteroides B-512F. The analogs studied were 2-deoxy-2-fluoro-α-D-glucopyranosyl fluoride, 3-deoxy-3-fluoro-a-D-glucopyranosyl fluoride, 3-deoxy-3-thio-°-D-glucopyranosyl fluoride, and 5-thio-α-D-glucopyranosyl fluoride. Kinetic constants for α-D-glucopyranosyl fluoride were also determined.

None of the α-D-glucopyranosyl fluorides were accepted as substrates for dextransucrase. 2-Deoxy-2-fluoro-α-D-glucopyranosyl fluoride, 3-deoxy-3-fgluoro-α-D-glucopyranosyl fluoride, and 3-deoxy-3-thio-α-D-glucopyranosyl fluoride were competitive inhibitors withKi values of 63, 93, and 53 mM, respectively. TheKm for α-D-glucopyranosyl fluoride was found to be 26 mM. The data indicate that the hydroxyl groups at C2 and C3 are important for proper binding of α-D-glucopyranosyl fluoride for the active site of dextransucrase and that the C3-hydroxyl probably acts as a hydrogen-bond donor.

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Authors and Affiliations

  1. Department of Chemical Engineering, University of California, 94720, Berkeley, CA

    Alan G. Michiels, Albert Y. Wang, Douglas S. Clark & Harvey W. Blanch

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  1. Alan G. Michiels
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  2. Albert Y. Wang
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  3. Douglas S. Clark
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  4. Harvey W. Blanch
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Michiels, A.G., Wang, A.Y., Clark, D.S. et al. Inhibition of dextransucrase by α-D-Glucose derivatives. Appl Biochem Biotechnol 31, 237–246 (1991). https://doi.org/10.1007/BF02921750

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  • DOI: https://doi.org/10.1007/BF02921750

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