Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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.
See this image and copyright information in PMC

References

    1. Yen PM. Physiol Rev. 2001;81(3):1097–1142. - PubMed
    1. Davis PJ, Leonard JL, Davis FB. Front Neuroendocrinol. 2008;29(2):211–218. - PubMed
    1. Scanlan TS, Suchland KL, Hart ME, Chiellini G, Huang Y, Kruzich PJ, Frascarelli S, Crossley DA, Bunzow JR, Ronca-Testoni S, Lin ET, Hatton D, Zucchi R, Grandy DK. Nat Med. 2004;10(6):638–642. - PubMed
    1. Saba A, Chiellini G, Frascarelli S, Marchini M, Ghelardoni S, Raffaelli A, Tonacchera M, Vitti P, Scanlan TS, Zucchi R. Endocrinology. 2010;151(10):5063–5073. - PubMed
    1. Braulke LJ, Klingenspor M, DeBarber A, Tobias SC, Grandy DK, Scanlan TS, Heldmaier GJ. Comp. Physiol. [B] 2008;178(2):167–177. - PubMed

LinkOut - more resources