Get access

Modeling of the 5′-Deiodination of Thyroxine by Iodothyronine Deiodinase: Chemical Corroboration of a Selenenyl Iodide Intermediate

Authors

  • Kei Goto Dr.,

    1. Interactive Research Center of Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-3543
    Search for more papers by this author
  • Daiju Sonoda,

    1. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    Search for more papers by this author
  • Keiichi Shimada Dr.,

    1. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    Search for more papers by this author
  • Shohei Sase Dr.,

    1. Interactive Research Center of Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-3543
    Search for more papers by this author
  • Takayuki Kawashima Prof. Dr.

    1. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    Search for more papers by this author

  • This work was supported by the Global COE Program (Chemistry) and Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology (Japan) and the Japan Society for the Promotion of Science. K.G. is grateful to Toray Science Foundation and The Society of Iodine Science for financial support. We also thank the Tosoh Finechem Corporation for the generous gifts of alkyllithium reagents.

Abstract

original image

Was macht eine gute Höhle aus? Ein molekularer Hohlraum ermöglichte die Stabilisierung eines Selenenyliodid(RSeI)-Intermediats, das bei der Abspaltung des 5′-Iodsubstituenten eines Thyroxinderivats mit einem Organoselenol entsteht (siehe Schema). Die für den Iodthyronin-Deiodinase-Katalysezyklus vorgeschlagenen chemischen Prozesse wurden experimentell bestätigt.

Ancillary