Synthesis and characterization of an epimer of tacrolimus, an immunosuppressive drug

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Dorthe Mondrup Skytte, Karla Andrea Frydenvang, Liselotte Hansen, Peter G Nielsen, Jerzy W Jaroszewski

8-Epitacrolimus (2), a new l-pipecolic acid macrolide lactone, was obtained by base-catalyzed epimerization of tacrolimus (FK-506, 1), an important immunosuppressive drug, and its structure determined by a single-crystal X-ray diffraction method. The compound was fully characterized by spectroscopic techniques. The epimer is of importance due to its potential biological effects as well as because of its possible formation during formulation, handling, and use of tacrolimus products.
Original languageEnglish
JournalJournal of Natural Products
Volume73
Issue number4
Pages (from-to)776-779
ISSN0163-3864
DOIs
Publication statusPublished - 18 Feb 2010

ID: 19367332