NaBH4 - A novel method for the deprotection of Nω-nitro-arginine

Mónika Sebestyén, György Kóczán, A. Csámpai, F. Hudecz

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The selective deprotection of Nω-nitro-arginine derivatives represents a major preparative challenge. This problem can be circumvented by the use of catalytic hydrogenation, but often high pressure, elevated temperature, and/or long reaction times are needed. In certain cases hydrogenation is not suitable, for example, small-scale reactions, parallel synthesis, or due to selectivity issues. Herein, we demonstrate for the first time, the use of NaBH4 in the presence of a metal ion catalyst for the removal of the Nω-nitro moiety under simple, 'open-vessel' conditions. This process using NaBH4 does not remove the benzyloxycarbonyl-protecting group; thus the method is orthogonal for this protecting scheme.

Original languageEnglish
Pages (from-to)546-548
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number5
DOIs
Publication statusPublished - Feb 3 2016

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Hydrogenation
Arginine
Metal ions
Metals
Ions
Derivatives
Pressure
Catalysts
Temperature

Keywords

  • Catalyst
  • N-Nitro-Arg deprotection
  • Selective removal
  • Sodium borohydride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

NaBH4 - A novel method for the deprotection of Nω-nitro-arginine. / Sebestyén, Mónika; Kóczán, György; Csámpai, A.; Hudecz, F.

In: Tetrahedron Letters, Vol. 57, No. 5, 03.02.2016, p. 546-548.

Research output: Contribution to journalArticle

Sebestyén, Mónika ; Kóczán, György ; Csámpai, A. ; Hudecz, F. / NaBH4 - A novel method for the deprotection of Nω-nitro-arginine. In: Tetrahedron Letters. 2016 ; Vol. 57, No. 5. pp. 546-548.
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