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. 2013;43(10):1439-1446.
doi: 10.1080/00397911.2011.639005. Epub 2012 Jun 5.

THE SYNTHESIS OF 13C9-15N-LABELED 3,5-DIIODOTHYRONINE AND THYROXINE

Sarah A Hackenmueller  1 , Thomas S Scanlan  1
Affiliations

THE SYNTHESIS OF 13C9-15N-LABELED 3,5-DIIODOTHYRONINE AND THYROXINE

Sarah A Hackenmueller et al. Synth Commun. 2013.

Abstract

Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Here we report the synthesis of 13C9-15N-T2 and 13C9-15N-T4, two labeled thyroid hormone derivatives suitable for in vivo LC-MS/MS studies.

Keywords: 13C9-15N-T2; 13C9-15N-T4; thyroid hormone; thyroxine.

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Figures

Figure 1
Figure 1
Structures of T4, 3,5-T2, and T1AM.
Scheme 1
Scheme 1
Reagents and conditions: (a), HCl, 2,2-dimethoxypropane; (b), BOC2O, NaHCO3, THF/H2O; (c), NIS, DCM; (d), 4-(triisopropyl)silyloxyphenyl boronic acid, Cu(OAc)2, DIPEA, pyridine, DCM; (e), TBAF, THF; (f), LiOH, MeOH/H2O; and (g), HCl, dioxane. An asterisk (*) indicates 13C or 15N.
Scheme 2
Scheme 2
Reagents and conditions: (a), ICl, BuNH2, 4:1 DCM/DMF; (b), LiOH, MeOH/H2O; and (c), HCl, dioxane. An asterisk (*) indicates 13C or 15N.
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