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

Goo Yoon, T. Mark Zabriskie, Hoon Cheon Seung

Research output: Contribution to journalArticle

1 Scopus citations

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
StatePublished - Feb 1 2009

Keywords

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

ASJC Scopus subject areas

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

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