doi: 10.1021/ja065950k.
The in vitro characterization of the iterative avermectin glycosyltransferase AveBI reveals reaction reversibility and sugar nucleotide flexibility
Affiliations
- PMID: 17177349
- DOI: 10.1021/ja065950k
Item in Clipboard
The in vitro characterization of the iterative avermectin glycosyltransferase AveBI reveals reaction reversibility and sugar nucleotide flexibility
J Am Chem Soc.
.
Abstract
The glycosyltransferase AveBI, which is involved in the biosynthesis of the macrolide antihelmintic avermectin (AVM), was characterized in vitro. AveBI was confirmed to catalyze two separate iterative additions of l-oleandrose, and the reversibility of AveBI-catalyzed reaction was also demonstrated. Investigation of sugar nucleotide specificity revealed 10 unique sugar nucleotide substrates which, in combination with five distinct aglycones, led to the production of 50 differentially glycosylated AVM variants.
Similar articles
-
Purification and identification of dTDP-oleandrose, the precursor of the oleandrose units of the avermectins.J Biol Chem. 1990 Oct 5;265(28):16965-70. J Biol Chem. 1990. PMID: 2211601
-
Insights about the biosynthesis of the avermectin deoxysugar L-oleandrose through heterologous expression of Streptomyces avermitilis deoxysugar genes in Streptomyces lividans.Chem Biol. 2001 Jul;8(7):681-700. doi: 10.1016/s1074-5521(01)00043-6. Chem Biol. 2001. PMID: 11451669
-
Engineering of avermectin biosynthetic genes to improve production of ivermectin in Streptomyces avermitilis.Bioorg Med Chem Lett. 2008 Oct 15;18(20):5359-63. doi: 10.1016/j.bmcl.2008.09.061. Epub 2008 Sep 19. Bioorg Med Chem Lett. 2008. PMID: 18824353
-
Glycosyltransferase-catalyzed synthesis of bioactive oligosaccharides.Biotechnol Adv. 2008 Sep-Oct;26(5):436-56. doi: 10.1016/j.biotechadv.2008.05.001. Epub 2008 May 15. Biotechnol Adv. 2008. PMID: 18565714 Review.
-
Recent progress in synthesis of carbohydrates with sugar nucleotide-dependent glycosyltransferases.Curr Opin Chem Biol. 2021 Apr;61:81-95. doi: 10.1016/j.cbpa.2020.10.007. Epub 2020 Dec 10. Curr Opin Chem Biol. 2021. PMID: 33310623 Free PMC article. Review.
Cited by
-
Asymmetric enzymatic glycosylation of mitoxantrone.Org Lett. 2011 May 20;13(10):2786-8. doi: 10.1021/ol200977u. Epub 2011 Apr 29. Org Lett. 2011. PMID: 21528870 Free PMC article.
-
Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation.Org Lett. 2012 Oct 5;14(19):5086-9. doi: 10.1021/ol3023374. Epub 2012 Sep 17. Org Lett. 2012. PMID: 22984807 Free PMC article.
-
Tracking down biotransformation to the genetic level: identification of a highly flexible glycosyltransferase from Saccharothrix espanaensis.Appl Environ Microbiol. 2013 Sep;79(17):5224-32. doi: 10.1128/AEM.01652-13. Epub 2013 Jun 21. Appl Environ Microbiol. 2013. PMID: 23793643 Free PMC article.
-
Biochemical and structural insights of the early glycosylation steps in calicheamicin biosynthesis.Chem Biol. 2008 Aug 25;15(8):842-53. doi: 10.1016/j.chembiol.2008.06.011. Chem Biol. 2008. PMID: 18721755 Free PMC article.
-
Synthetic Biology in Natural Product Biosynthesis.Chem Rev. 2025 Apr 9;125(7):3814-3931. doi: 10.1021/acs.chemrev.4c00567. Epub 2025 Mar 21. Chem Rev. 2025. PMID: 40116601 Review.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
