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Methionine anchoring applied to the solid-phase synthesis of lysine-containing 'head-to-tail' cyclic peptides

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Abstract

Lysine-containing 'head-to-tail' cyclic peptides can be prepared via a side-chain anchoring solid-phase synthesis strategy. A handle is prepared using a methionine residue, the C α-carboxylof which forms an amide with the N ε-amine of lysine. Subsequently, the linear peptide sequence is assembled, appropriatedeblocking steps are carried out, and on-resin head-to-tail cyclizationfollows. Optionally, acid-labile protecting groups may be removed while the peptide remains resin-bound. The final cleavage step uses CNBr, and releases the free or protected cyclic peptide into solution.

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Author notes

  1. Joseph C. Kappel

    Present address: Laboratoire des Aminoacides, Peptides et Protéines (LAPP), UMR 5810 CNRS, Universités Montpellier I et II, Faculté de Pharmacie, 15 Avenue Charles Flahault, BP 14491, 34093, Montpellier Cédex 5, France

Authors and Affiliations

  1. Department of Chemistry, University of Minnesota, 207 Pleasant St. S.E., Minneapolis, MN, 55455, U.S.A. Present address

    Joseph C. Kappel & George Barany

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  1. Joseph C. Kappel
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  2. George Barany
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Correspondence to George Barany.

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Kappel, J.C., Barany, G. Methionine anchoring applied to the solid-phase synthesis of lysine-containing 'head-to-tail' cyclic peptides. Letters in Peptide Science 10, 119–125 (2003). https://doi.org/10.1023/B:LIPS.0000032376.71038.f7

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  • DOI: https://doi.org/10.1023/B:LIPS.0000032376.71038.f7

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