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Solid-phase synthesis of reduced selenocysteine tetrapeptides and their oxidized analogs containing selenenylsulfide eight-membered rings

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Abstract

A series of protected and reduced forms of model tetrapeptides that mimic the C-terminus of human thioredoxin reductases were obtained in good yields, using solid-phase peptide synthesis (SPPS). SPPS was performed on the Knorr Amide MBHA resin for Fmoc chemistry using especially protected cystein and selenocystein derivatives. All amino acids have been coupled according to the HBTU/HOBt/DIPEA method. Furthermore, the corresponding oxidized peptides containing eight-membered rings with intramolecular S–S and S–Se bridges were prepared via I\(_{2}\)/MeOH or DMSO/TFA oxidation, respectively.

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Acknowledgments

We thank the DFG for funding this research as part of the priority program “Selenoproteins”, Grant WE 1467/4-2.

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Authors and Affiliations

  1. Leibniz-Institut für Pflanzenbiochemie, Weinberg 3, 06120 , Halle (Saale), Germany

    Ludger A. Wessjohann, Alex Schneider, Goran N. Kaluđerović & Wolfgang Brandt

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  1. Ludger A. Wessjohann
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  2. Alex Schneider
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  3. Goran N. Kaluđerović
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  4. Wolfgang Brandt
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Correspondence to Ludger A. Wessjohann.

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Wessjohann, L.A., Schneider, A., Kaluđerović, G.N. et al. Solid-phase synthesis of reduced selenocysteine tetrapeptides and their oxidized analogs containing selenenylsulfide eight-membered rings. Mol Divers 17, 537–545 (2013). https://doi.org/10.1007/s11030-013-9454-x

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  • DOI: https://doi.org/10.1007/s11030-013-9454-x

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