Synthesis of [guanido-13C]-γ-hydroxyarginine

Goo Yoon, Mark Zabriskie, Hoon Cheon Seung

Research output: Contribution to journalArticle

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Abstract

This report describes an efficient method of synthesizing [guanido- 13C]-γ-hydroxyarginine HCl salt. Iodolactonization of N-Boc-protected allylglycine mainly provided the cis iodo compound 2. This was converted to an amine through azide 4. The amine 5 was reacted with N-Boc-protected [13C]thiourea to afford N-Boc-protected [ 13C]guanidine 6, which underwent base catalyzed ring opening. Removal of the N-Boc group afforded [guanido-13C]-γ-hydroxyarginine HCl salt 7 giving a 30% overall yield of the final product from N-Boc protected allylglycine 1 in five steps.

Original languageEnglish (US)
Pages (from-to)53-55
Number of pages3
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume52
Issue number2
DOIs
Publication statusPublished - Feb 2009
Externally publishedYes

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Keywords

  • [Guanido-C]-γ-hydroxyarginine
  • Carbon-13 synthesis
  • Iodolactonization

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Spectroscopy
  • Drug Discovery
  • Radiology Nuclear Medicine and imaging
  • Biochemistry

Cite this

Synthesis of [guanido-13C]-γ-hydroxyarginine. / Yoon, Goo; Zabriskie, Mark; Seung, Hoon Cheon.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 52, No. 2, 02.2009, p. 53-55.

Research output: Contribution to journalArticle