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Volumn 128, Issue 51, 2006, Pages 16420-16421

The in vitro characterization of the iterative avermectin glycosyltransferase AveBI reveals reaction reversibility and sugar nucleotide flexibility

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; AVERMECTIN; AVERMECTIN GLYCOSYLTRANSFERASE; CARBOHYDRATE; GLYCOSYLTRANSFERASE; MACROLIDE; SUGAR NUCLEOTIDE; UNCLASSIFIED DRUG;

EID: 33845935524     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065950k     Document Type: Article
Times cited : (75)

References (30)
  • 1
    • 26844575149 scopus 로고    scopus 로고
    • For recent reviews see: a
    • For recent reviews see: (a) Geary, T. G. Trends Parasitol. 2005, 21, 530-532.
    • (2005) Trends Parasitol , vol.21 , pp. 530-532
    • Geary, T.G.1
  • 6
    • 22544467806 scopus 로고    scopus 로고
    • Some other potential examples include members of the angucycline, aureolic acid and orthosomycin families (e.g., see Luzhetskyy, A.; Fedoryshyn, M.; Durr, C.; Taguchi, T.; Novikov, V.; Bechthold, A. Chem. Biol. 2005, 12, 725-729.).
    • Some other potential examples include members of the angucycline, aureolic acid and orthosomycin families (e.g., see Luzhetskyy, A.; Fedoryshyn, M.; Durr, C.; Taguchi, T.; Novikov, V.; Bechthold, A. Chem. Biol. 2005, 12, 725-729.).
  • 15
    • 33845949514 scopus 로고    scopus 로고
    • +2.
    • +2.
  • 18
    • 0034856716 scopus 로고    scopus 로고
    • The synthesis of TDP-β-L-oleandrose has not been reported, and the chemoenzymatic synthesis of the closest related sugar nucleotide (TDP-β-L-olivose, which lacks the sugar 3́-OMe) required six linear steps with an overall reported yield of 20% (Amann, S.; Drager, G.; Rupprath, C.; Kirschning, A.; Elling, L. Carbohydr. Res. 2001, 335, 23-32.).
    • The synthesis of TDP-β-L-oleandrose has not been reported, and the chemoenzymatic synthesis of the closest related sugar nucleotide (TDP-β-L-olivose, which lacks the sugar 3́-OMe) required six linear steps with an overall reported yield of 20% (Amann, S.; Drager, G.; Rupprath, C.; Kirschning, A.; Elling, L. Carbohydr. Res. 2001, 335, 23-32.).
  • 19
    • 33845949513 scopus 로고    scopus 로고
    • 2. Reversibility of AveBI reaction was assayed by co-incubation of 100 μM avermectin Bla (1) or ivermectin (7) and 2 mM TDP with 12 μM AveBI at 30 °C overnight.
    • 2. Reversibility of AveBI reaction was assayed by co-incubation of 100 μM avermectin Bla (1) or ivermectin (7) and 2 mM TDP with 12 μM AveBI at 30 °C overnight.
  • 20
    • 33845945948 scopus 로고    scopus 로고
    • The AveBI-catalyzed aglycone exchange reaction was assayed by co-incubation of 100 μM 1, 100 μM 5, and 2 mM TDP with 12 μM AveBI at 30 0C overnight.
    • (b) The AveBI-catalyzed aglycone exchange reaction was assayed by co-incubation of 100 μM 1, 100 μM 5, and 2 mM TDP with 12 μM AveBI at 30 0C overnight.
  • 21
    • 0037109032 scopus 로고    scopus 로고
    • The sugar nucleotides for this study were generated as previously described, (a) Barton, W. A.; Biggins, J. B.; Jiang, J.; Thorson, J. S.; Nikolov, D. B. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13397-13402.
    • The sugar nucleotides for this study were generated as previously described, (a) Barton, W. A.; Biggins, J. B.; Jiang, J.; Thorson, J. S.; Nikolov, D. B. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13397-13402.
  • 28
    • 33845964688 scopus 로고    scopus 로고
    • A typical reaction to assess sugar nucleotide specificity contained 50 μM algycon (1-3. 5-8.), approximately 300 μM TDP-sugar and 12 μM AveBI incubated at 30 °C overnight.
    • A typical reaction to assess sugar nucleotide specificity contained 50 μM algycon (1-3. 5-8.), approximately 300 μM TDP-sugar and 12 μM AveBI incubated at 30 °C overnight.


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