PROTON NUCLEAR MAGNETIC-RESONANCE ASSIGNMENTS OF THYROID-HORMONE AND ITS ANALOGS

  • 1 January 1985
    • journal article
    • research article
    • Vol. 10  (5) , 803-811
Abstract
1H NMR data of a series of thyroid hormone analogs, e.g., thyroxine (T4), 3,5,,3''-triiodothyronine (T3), 3,3'',5''-triiodothyronine (rT3), 3,3''-diiodothyronine (3,3''-T2), 3,5-diiodothyronine (3,5-T2), 3'',5''-diiodothyronine (3'',5''-T2), 3-monoiodothyronine (3-T1), 3''-monoiodothyronine (3''-T1) and thyronine (T0) in dimethylsufoxide (DMSO) were obtained on a 300 MHz spectrometer. The chemical shift and coupling constant are determined and tabulated for each aromatic proton. The inner tyrosyl ring protons in T4, T3 and 3,5-T2 have downfield chemical shifts with respect to those of the outer phenolic ring protons. Four-bond cross-ring coupling was observed in all the monoiodinated rings. This long-range coupling does not exist in T4, diiodinated on both rings, and T0, containing no iodines on the rings. There is no evidence that at 30.degree. C these iodothyronines have any motional constraint in DMSO solution. In addition to identification of the hormones, the potential use of some characteristic peaks as probes in binding studies is discussed.

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