3
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: not found

      P450 BM3-Catalyzed Regio- and Stereoselective Hydroxylation Aiming at the Synthesis of Phthalides and Isocoumarins.

      Read this article at

      ScienceOpenPublisherPubMed
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          Cytochrome P450 BM3 monooxygenases are able to catalyze the regio- and stereoselective oxygenation of a broad range of substrates, with promising potential for synthetic applications. To study the suitability of P450 BM3 variants for stereoselective benzylic hydroxylation of 2-alkylated benzoic acid esters, the biotransformation of methyl 2-ethylbenzoate, resulting in both enantiomeric forms of 3-methylphthalide, was investigated. In the case of methyl 2-propylbenzoate as a substrate the regioselectivity of the reaction was shifted towards β-hydroxylation, resulting in the synthesis of enantioenriched R- and S-configured 3-methylisochroman-1-one. The potential of P450 BM3 variants for regio- and stereoselective synthesis of phthalides and isocoumarins offers a new route to a class of compounds that are valuable synthons for a variety of natural compounds.

          Related collections

          Author and article information

          Journal
          Chembiochem
          Chembiochem : a European journal of chemical biology
          Wiley
          1439-7633
          1439-4227
          April 04 2017
          : 18
          : 7
          Affiliations
          [1 ] Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf, Forschungszentrum Jülich, Stetternicher Forst, Gebäude 15.8, 52426, Jülich, Germany.
          [2 ] Institut für Bio- und Geowissenschaften (IBG-1: Biotechnologie), Forschungszentrum Jülich, 52426, Jülich, Germany.
          Article
          10.1002/cbic.201600685
          28107587
          3c5da50a-d7d8-49ec-b0b2-a17ca96c0816
          History

          P450 enzymes,C−H activation,benzylic hydroxylation,biotransformations,protein engineering

          Comments

          Comment on this article