Crystal structure and mechanism of a bacterial fluorinating enzyme (original) (raw)

• O'Hagan, D. & Harper, D. B. Fluorine-containing natural products. J. Chem. 100, 127–133 (1999)
  CAS Google Scholar
• Xu, X.-H. et al. 5-Fluorouracil derivatives from the sponge Phakellia fusca. J. Nat. Prod. 66, 285–288 (2003)
  Article CAS Google Scholar
• vanPee, K. H. Biosynthesis of halogenated metabolites by bacteria. Annu. Rev. Microbiol. 50, 375–399 (1996)
  Article CAS Google Scholar
• Littlechild, J. Haloperoxidases and their role in biotransformation reactions. Curr. Opin. Chem. Biol. 3, 28–34 (1999)
  Article CAS Google Scholar
• Sandford, G. Organofluorine chemistry. Phil. Trans. R. Soc. Lond. A 358, 455–471 (2000)
  Article ADS CAS Google Scholar
• Mann, J. Modern methods for the introduction of fluorine into organic molecules—an approach to compounds with altered chemical and biological activities. Chem. Soc. Rev. 16, 381–436 (1987)
  Article ADS CAS Google Scholar
• Hutchinson, J. & Sandford, G. Elemental fluorine in organic chemistry. Top. Curr. Chem. 193, 1–43 (1997)
  Article CAS Google Scholar
• Zechel, D. L. et al. Enzymatic synthesis of carbon–fluorine bonds. J. Am. Chem. Soc. 123, 4350–4351 (2001)
  Article CAS Google Scholar
• Sanada, M. et al. Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya. J. Antibiotics 141, 259–265 (1986)
  Article Google Scholar
• O'Hagan, D., Schaffrath, C., Cobb, S. L., Hamilton, J. T. G. & Murphy, C. D. Enzyme catalysed organofluorine synthesis. Nature 416, 279 (2002)
  Article ADS CAS Google Scholar
• Schaffrath, C., Deng, H. & O'Hagan, D. Isolation and characterisation of 5′-fluorodeoxyadenosine synthetase, a fluorination enzyme from Streptomyces cattleya. FEBS Lett. 547, 111–114 (2003)
  Article CAS Google Scholar
• Boutselakis, H. et al. E-MSD: the European Bioinformatics Institute Macromolecular Structure Database. Nucleic Acids Res. 31, 458–462 (2003)
  Article CAS Google Scholar
• Holm, L. & Sander, C. Protein folds and families: sequence and structure alignments. Nucleic Acids Res. 27, 244–247 (1999)
  Article CAS Google Scholar
• Bateman, A. et al. The Pfam Protein Families Database. Nucleic Acids Res. 30, 276–280 (2002)
  Article CAS Google Scholar
• Altschul, S. F. et al. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 25, 3389–3402 (1997)
  Article CAS Google Scholar
• Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr. B 58, 380–388 (2002)
  Article Google Scholar
• Berman, H. M. et al. The Protein Data Bank. Acta Crystallogr. D 58, 899–907 (2002)
  Article Google Scholar
• Kollman, P. A. et al. Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models. Acc. Chem. Res. 33, 889–897 (2000)
  Article CAS Google Scholar
• O'Hagan, D. et. al. An assay for the enantiomeric assay of [2H1]-fluoroacetic acid: Insight into the stereochemical course of fluorination during fluorometabolite biosynthesis in Streptomyces cattleya. J. Am. Chem. Soc. 125, 379–387 (2003)
  Article CAS Google Scholar
• Dunitz, J. & Taylor, R. Organic fluorine hardly ever accepts hydrogen bonds. Chem. Eur. J. 3, 89–98 (1997)
  Article CAS Google Scholar
• Howard, J. A. K., Hoy, J. V., O'Hagan, D. & Smith, G. T. How good is fluorine as a hydrogen bond acceptor? Tetrahedron 38, 12613–12622 (1996)
  Article Google Scholar
• Smart, O. S., Neduvelil, J. G., Wang, X., Wallace, B. A. & Sansom, M. S. P. HOLE: A program for the analysis of the pore dimensions of ion channel structural models. J. Mol. Graph. Model 14, 354–360 (1996)
  Article CAS Google Scholar
• Dong, C. et al. Crystallization and X-ray diffraction of the 5′-fluoro-5′-deoxyadenosine synthase, a fluorination enzyme from Streptomyces cattleya. Acta Crystallogr. D 60, 760–763 (2003)
  Google Scholar
• Doublie, S. Preparation of selenomethionyl proteins for phase determination. Methods Enzymol. 276, 523–530 (1997)
  Article CAS Google Scholar
• Bailey, S. The CCP4 Suite—programs for protein crystallography. Acta Crystallogr. D 50, 760–763 (1994)
  Article Google Scholar
• Terwilliger, T. C. & Berendzen, J. Automated MAD and MIR structure solution. Acta Crystallogr. D 55, 849–861 (1999)
  Article CAS Google Scholar
• Morris, R. J., Perrakis, A. & Lamzin, V. S. ARP/wARP's model-building algorithms. I. The main chain. Acta Crystallogr. D 58, 968–975 (2002)
  Article Google Scholar
• Murshudov, G. N., Vagin, A. A., Lebedev, A., Wilson, K. S. & Dodson, E. J. Efficient anisotropic refinement of macromolecular structures using FFT. Acta Crystallogr. D 55, 247–255 (1999)
  Article CAS Google Scholar
• van Aalten, D. M. F. et al. PRODRG, a program for generating molecular topologies and unique molecular descriptors from coordinates of small molecules. J. Comput. Aided Mol. Des. 10, 255–262 (1996)
  Article ADS CAS Google Scholar
• Schaffrath, C., Cobb, S. L. & O'Hagan, D. Cell-free biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. Angew. Chem. Int. Edn Engl. 41, 3913–3915 (2002)
  Article CAS Google Scholar
• DeLano, W. L., The PyMOL Molecular Graphics System 〈http://www.pymol.org/〉 (2003).