The Formation of Pyrroline and Tetrahydropyridine Rings in Amino Acids Catalyzed by Pyrrolysine Synthase (PylD)
KAUST Grant NumberFIC/2010/07
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AbstractThe dehydrogenase PylD catalyzes the ultimate step of the pyrrolysine pathway by converting the isopeptide L-lysine-Nε-3R-methyl-D-ornithine to the 22nd proteinogenic amino acid. In this study, we demonstrate how PylD can be harnessed to oxidize various isopeptides to novel amino acids by combining chemical synthesis with enzyme kinetics and X-ray crystallography. The data enable a detailed description of the PylD reaction trajectory for the biosynthesis of pyrroline and tetrahydropyridine rings as constituents of pyrrolysine analogues. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
CitationQuitterer F, Beck P, Bacher A, Groll M (2014) The Formation of Pyrroline and Tetrahydropyridine Rings in Amino Acids Catalyzed by Pyrrolysine Synthase (PylD). Angew Chem Int Ed 53: 8150–8153. Available: http://dx.doi.org/10.1002/anie.201402595.
SponsorsThis work was supported by the Hans-Fischer-Gesellschaft, by Award No. FIC/2010/07 from KAUST, and by the Deutsche Forschungsgemeinschaft (DFG, grant GR1861/7-1).
CollectionsPublications Acknowledging KAUST Support
- The complete biosynthesis of the genetically encoded amino acid pyrrolysine from lysine.
- Authors: Gaston MA, Zhang L, Green-Church KB, Krzycki JA
- Issue date: 2011 Mar 31
- Biosynthesis of the 22nd genetically encoded amino acid pyrrolysine: structure and reaction mechanism of PylC at 1.5Å resolution.
- Authors: Quitterer F, List A, Beck P, Bacher A, Groll M
- Issue date: 2012 Dec 14
- D-Ornithine coopts pyrrolysine biosynthesis to make and insert pyrroline-carboxy-lysine.
- Authors: Cellitti SE, Ou W, Chiu HP, Grünewald J, Jones DH, Hao X, Fan Q, Quinn LL, Ng K, Anfora AT, Lesley SA, Uno T, Brock A, Geierstanger BH
- Issue date: 2011 Apr 27
- The path of lysine to pyrrolysine.
- Authors: Krzycki JA
- Issue date: 2013 Aug
- Structure and reaction mechanism of pyrrolysine synthase (PylD).
- Authors: Quitterer F, Beck P, Bacher A, Groll M
- Issue date: 2013 Jul 1