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 language | English |
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Pages (from-to) | 70-79 |
Number of pages | 10 |
Journal | Journal of Peptide Research |
Volume | 56 |
Issue number | 2 |
DOIs | |
Publication status | Published - 2000 |
Externally published | Yes |
Keywords
- 2-(4-nitrophenylsulfonyl)ethoxycarbonyl
- Base- labile
- Fmoc
- MSH
- Melanotropin
- Nsc
- Peptide
- Protecting group
- Solid- phase
- Synthesis