Evaluation of new base-labile 2-(4-nitrophenylsulfonyl) ethoxycarbonyl (Nsc)-amino acids for solid-phase peptide synthesis

P. M. Balse, H. J. Kim, G. Han, Victor J. Hruby

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The 2-(4-nitrophenylsulfonyl)ethoxycarbonyl (Nsc) group is a new base- labile protecting group for solid-phase peptide synthesis, completely interchangeable with the fluorenylmethoxycarbonyl (Fmoc) protecting group, but with certain advantages. In this paper, we report a methodology with N(α)-Nsc-protected amino acids for the synthesis of some melanotropins important to our research, namely, γ-melanocyte-stimulating hormone (γ- MSH), its [Nle3]-analogue, and a cyclic α-MSH/β-MSH hybrid. We developed an efficient protocol for the synthesis of the cyclic MSH analogue that yielded this peptide in >98% purity. The γ-MSH synthesis, which gave problems with both the Boc and Fmoc strategies, yielded the desired peptide by Nsc-chemistry but was accompanied by side products. Finally, the Nle3-γ- MSH analogue was synthesized more efficiently using the Fmoc strategy, suggesting that Nsc-chemistry might not be the best methodology for certain sequences.

Original languageEnglish (US)
Pages (from-to)70-79
Number of pages10
JournalJournal of Peptide Research
Volume56
Issue number2
DOIs
StatePublished - Aug 19 2000

Keywords

  • 2-(4-nitrophenylsulfonyl)ethoxycarbonyl
  • Base- labile
  • Fmoc
  • MSH
  • Melanotropin
  • Nsc
  • Peptide
  • Protecting group
  • Solid- phase
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology

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