A facile and convenient synthesis of boc-protected 5-carboxyspermine

Jong Soo Choi, Jae Won Park, Bieong Kil Kim, Kyung Oh Doh, Young Bae Seu

Research output: Contribution to journalArticlepeer-review

Abstract

Gene therapy is a powerful technology for treating incurable and hereditary disease in humans. In the recent years, a lot of studies have been done on the development of DNA carriers. Non-viral vectors, like liposomes, polymers, and micelles, has become common vehicles due to their safety. The key compound of DOGS, DOSPA and DOSPER is the 5-carboxyspermine which formed the poly amine head-group and carries four positive charges. In general, multivalent head-group shows more transfection efficiency than monovalent analogues. In this paper, the efficient and simple synthesis of Boc-protected 5-carboxyspermine is described. Boc-protected polyamines were synthesized from (S)-2,5-diaminopentanoic acid monohydrochloride (L-ornithine) monohydrochloride through both cyanoethylation and direct catalytic reduction of nitriles with the combination of nickel (II) chloride, sodium borohydride and di-tert-butyl decarbonate (BOC2O) in a one-pot two-reaction.

Original languageEnglish
Pages (from-to)615-618
Number of pages4
JournalLetters in Organic Chemistry
Volume16
Issue number8
DOIs
StatePublished - 2019

Keywords

  • 5-carboxyspermine
  • Boc protection
  • Cationic lipids
  • Cyanoethylation
  • Nitrile reduction
  • Polyamines

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