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Cited by 36

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Investigating Substrate Scope and Enantioselectivity of a Defluorinase by a Stereochemical Probe

Wang, Jian-bo, Ilie, Adriana, Yuan, Shuguang, Reetz, Manfred T.·2017·Journal of the American Chemical Society
DOI 10.1021/jacs.7b06019
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Abstract

The possibility of a double Walden inversion mechanism of the fluoracetate dehalogenase FAcD (RPA1163) has been studied by subjecting rac-2-fluoro-2-phenyl acetic acid to the defluorination process. This stereochemical probe led to inversion of configuration in a kinetic resolution with an extremely high selectivity factor (E > 500), showing that the classical mechanism involving S N 2 reaction by Asp110 pertains. The high preference for the (S)-substrate is of synthetic value. Wide substrate scope of RPA1163 in such hydrolytic kinetic resolutions can be expected because the reaction of the even more sterically demanding rac-2-fluoro-2-benzyl acetic acid proceeded similarly. Substrate acceptance and stereoselectivity were explained by extensive molecular modeling (MM) and molecular dynamics (MD) computations. These computations were also applied to fluoroacetic acid itself, leading to further insights.

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Research works printed but not linked: 73

  1. Banks R. E., 2013, Organofluorine Chemistry: Principles and Commercial Applications
  2. Ojima I., 2009, Fluorine in Medicinal Chemistry and Chemical Biology, 10.1002/9781444312096 · DOI
  3. Reddy V. P., 2015, Organofluorine Compounds in Biology and Medicine
  4. 10.1021/acs.chemrev.5b00392 · DOI
  5. 10.1039/C6CS00351F · DOI
  6. 10.1016/j.jfluchem.2014.06.014 · DOI
  7. Gouverneur V., 2012, Fluorine in Pharmaceutical and Medicinal Chemistry, 10.1142/p746 · DOI
  8. 10.1039/B711844A · DOI
  9. 10.1038/nature10108 · DOI
  10. 10.1021/acs.chemrev.5b00493 · DOI
  11. 10.1039/C4QO00078A · DOI
  12. 10.1016/j.tetlet.2014.06.006 · DOI
  13. 10.1039/C4DT03410D · DOI
  14. 10.1246/bcsj.20160223 · DOI
  15. 10.1039/C6OB01087C · DOI
  16. 10.1021/jacs.6b12911 · DOI
  17. 10.1007/s00253-016-7304-3 · DOI
  18. 10.1016/j.chemosphere.2011.09.054 · DOI
  19. 10.1021/cr500209t · DOI · Paper page
  20. 10.1021/ar500415c · DOI
  21. 10.3389/fchem.2014.00098 · DOI
  22. 10.1021/np900719u · DOI
  23. 10.1517/17425255.2015.1020295 · DOI
  24. 10.1016/0045-2068(84)90003-8 · DOI
  25. 10.1016/S1381-1177(03)00098-5 · DOI · Paper page
  26. 10.1016/j.jfluchem.2004.12.001 · DOI
  27. 10.1126/science.164.3884.1123 · DOI
  28. 10.1074/jbc.273.47.30897 · DOI · Paper page
  29. 10.1002/tcr.20141 · DOI
  30. 10.1128/JB.183.17.5058-5066.2001 · DOI
  31. 10.1016/j.sbi.2003.10.009 · DOI
  32. 10.1002/biot.201100486 · DOI
  33. 10.1007/s00253-015-6954-x · DOI
  34. 10.1126/science.aag2355 · DOI
  35. 10.1002/cber.18930260146 · DOI
  36. 10.1002/cber.18960290127 · DOI
  37. 10.1002/cber.18990320277 · DOI
  38. 10.1039/tf9383400202 · DOI
  39. 10.1039/JR9280002447 · DOI
  40. 10.1021/ja01182a113 · DOI
  41. 10.1055/s-0034-1380511 · DOI
  42. 10.1021/jo060316a · DOI
  43. 10.1016/S0040-4039(99)00534-1 · DOI
  44. 10.1016/j.bmcl.2011.10.094 · DOI
  45. 10.1039/a606820k · DOI
  46. 10.1002/poc.526 · DOI
  47. 10.1039/b517461a · DOI
  48. 10.1039/B714118A · DOI
  49. 10.1021/ja00723a042 · DOI
  50. 10.1021/jo00952a047 · DOI
  51. 10.1039/C39820000362 · DOI
  52. 10.1021/ja00389a064 · DOI
  53. 10.1517/17460441.2015.1032936 · DOI
  54. 10.1038/srep34736 · DOI
  55. 10.1016/S0957-4166(01)00034-9 · DOI
  56. 10.1021/ol4009377 · DOI
  57. 10.1002/anie.200704651 · DOI
  58. 10.1016/j.tetasy.2014.06.015 · DOI
  59. Eswar N., 2007, Current Protocols in Protein Science
  60. 10.1021/ct900587b · DOI
  61. 10.1021/ct200133y · DOI
  62. 10.1007/s10822-010-9349-1 · DOI
  63. 10.1021/jm0306430 · DOI · Paper page
  64. 10.1093/bioinformatics/btt055 · DOI
  65. 10.1002/prot.24350 · DOI
  66. 10.1002/jcc.20035 · DOI
  67. 10.1186/1756-0500-5-367 · DOI
  68. 10.1002/jcc.540161003 · DOI
  69. 10.1016/0263-7855(96)00018-5 · DOI · Paper page
  70. 10.1016/j.str.2016.11.012 · DOI
  71. 10.1002/wcms.1298 · DOI
  72. 10.1093/nar/gkv315 · DOI
  73. 10.1021/ci600342e · DOI

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Metadata

Authors
Wang, J.-B., Ilie, A., Yuan, S., & Reetz, M. T.
Affiliations
  • Department of Chemistry, Philipps-University, Hans-Meerwein-Strasse 4, 35032 Marburg, Germany
  • Laboratory of Physical Chemistry of Polymers and Membranes, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH B3 495 (Bâtiment CH) Station 6, CH-1015 Lausanne, Switzerland
ORCID
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2017-08-07
Volume
139
Issue
32
Pages
11241-11247
ISSN
  • 0002-7863
  • 1520-5126
DOI
10.1021/jacs.7b06019
Cited by
36
References
2
Language
en
Funders
Max-Planck-Gesellschaft

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