Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions - PubMed (original) (raw)
. 2006 Sep 1;313(5791):1291-4.
doi: 10.1126/science.1130028.
Affiliations
- PMID: 16946071
- DOI: 10.1126/science.1130028
Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions
Changsheng Zhang et al. Science. 2006.
Abstract
Glycosyltransferases (GTs), an essential class of ubiquitous enzymes, are generally perceived as unidirectional catalysts. In contrast, we report that four glycosyltransferases from two distinct natural product biosynthetic pathways-calicheamicin and vancomycin-readily catalyze reversible reactions, allowing sugars and aglycons to be exchanged with ease. As proof of the broader applicability of these new reactions, more than 70 differentially glycosylated calicheamicin and vancomycin variants are reported. This study suggests the reversibility of GT-catalyzed reactions may be general and useful for generating exotic nucleotide sugars, establishing in vitro GT activity in complex systems, and enhancing natural product diversity.
Similar articles
- Biochemical and structural insights of the early glycosylation steps in calicheamicin biosynthesis.
Zhang C, Bitto E, Goff RD, Singh S, Bingman CA, Griffith BR, Albermann C, Phillips GN Jr, Thorson JS. Zhang C, et al. 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. - Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: interactions with acceptor and nucleotide ligands.
Mulichak AM, Lu W, Losey HC, Walsh CT, Garavito RM. Mulichak AM, et al. Biochemistry. 2004 May 11;43(18):5170-80. doi: 10.1021/bi036130c. Biochemistry. 2004. PMID: 15122882 - Glyco-stripping and glyco-swapping.
Melançon CE 3rd, Thibodeaux CJ, Liu HW. Melançon CE 3rd, et al. ACS Chem Biol. 2006 Sep 19;1(8):499-504. doi: 10.1021/cb600365q. ACS Chem Biol. 2006. PMID: 17168536 - Discovery and molecular engineering of sugar-containing natural product biosynthetic pathways in actinomycetes.
Oh TJ, Mo SJ, Yoon YJ, Sohng JK. Oh TJ, et al. J Microbiol Biotechnol. 2007 Dec;17(12):1909-21. J Microbiol Biotechnol. 2007. PMID: 18167436 Review. - Features and applications of bacterial glycosyltransferases: current state and prospects.
Luzhetskyy A, Bechthold A. Luzhetskyy A, et al. Appl Microbiol Biotechnol. 2008 Oct;80(6):945-52. doi: 10.1007/s00253-008-1672-2. Epub 2008 Sep 6. Appl Microbiol Biotechnol. 2008. PMID: 18777021 Review.
Cited by
- Functional characterization and structural basis of a reversible glycosyltransferase involves in plant chemical defence.
Cheng W, Fang X, Guan Z, Yao Y, Xu Z, Bi Y, Ren K, Li J, Chen F, Chen X, Ma W, Chu Z, Deng Z, Zhang Z, Lu L. Cheng W, et al. Plant Biotechnol J. 2023 Dec;21(12):2611-2624. doi: 10.1111/pbi.14157. Epub 2023 Aug 15. Plant Biotechnol J. 2023. PMID: 37581303 Free PMC article. - Increasing carbohydrate diversity via amine oxidation: aminosugar, hydroxyaminosugar, nitrososugar, and nitrosugar biosynthesis in bacteria.
Timmons SC, Thorson JS. Timmons SC, et al. Curr Opin Chem Biol. 2008 Jun;12(3):297-305. doi: 10.1016/j.cbpa.2008.03.017. Epub 2008 Apr 18. Curr Opin Chem Biol. 2008. PMID: 18424273 Free PMC article. Review. - Validation of a metabolite-GWAS network for Populus trichocarpa family 1 UDP-glycosyltransferases.
Saint-Vincent PMB, Furches A, Galanie S, Teixeira Prates E, Aldridge JL, Labbe A, Zhao N, Martin MZ, Ranjan P, Jones P, Kainer D, Kalluri UC, Chen JG, Muchero W, Jacobson DA, Tschaplinski TJ. Saint-Vincent PMB, et al. Front Plant Sci. 2023 Jul 21;14:1210146. doi: 10.3389/fpls.2023.1210146. eCollection 2023. Front Plant Sci. 2023. PMID: 37546246 Free PMC article. - Catalytic flexibility of rice glycosyltransferase OsUGT91C1 for the production of palatable steviol glycosides.
Zhang J, Tang M, Chen Y, Ke D, Zhou J, Xu X, Yang W, He J, Dong H, Wei Y, Naismith JH, Lin Y, Zhu X, Cheng W. Zhang J, et al. Nat Commun. 2021 Dec 2;12(1):7030. doi: 10.1038/s41467-021-27144-4. Nat Commun. 2021. PMID: 34857750 Free PMC article. - Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions.
Gantt RW, Peltier-Pain P, Cournoyer WJ, Thorson JS. Gantt RW, et al. Nat Chem Biol. 2011 Aug 21;7(10):685-91. doi: 10.1038/nchembio.638. Nat Chem Biol. 2011. PMID: 21857660 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials
Miscellaneous