Synthesis and characterization of an epimer of tacrolimus, an immunosuppressive drug.
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.
Skytte
Dorthe M
DM
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
Frydenvang
Karla
K
Hansen
Liselotte
L
Nielsen
Peter G
PG
Jaroszewski
Jerzy W
JW
D018360:Crystallography, X-Ray; D007166:Immunosuppressive Agents / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D016559:Tacrolimus / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D007166:Immunosuppressive Agents; D016559:Tacrolimus