Preparation of the β2-Homoselenocysteine Derivatives Fmoc-(S)-β2hSec(PMB)-OH and Boc-(S)-β2hSec(PMB)-OH for Solution and Solid-Phase Peptide Synthesis

Authors

  • Krystyna Patora-Komisarska,

    1. Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule, ETH-Zürich, Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich (phone: +41-44-632 29 90; fax: +41-44-632 11 44)
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    • Postdoctoral Fellows at ETH-Zürich financed by grants from the Swiss National Science Foundation (200020-117586, 200020-126693), and by Novartis Pharma AG, Basel.

  • Dominika Jadwiga Podwysocka,

    1. Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule, ETH-Zürich, Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich (phone: +41-44-632 29 90; fax: +41-44-632 11 44)
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    • Postdoctoral Fellows at ETH-Zürich financed by grants from the Swiss National Science Foundation (200020-117586, 200020-126693), and by Novartis Pharma AG, Basel.

  • Dieter Seebach

    Corresponding author
    1. Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule, ETH-Zürich, Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich (phone: +41-44-632 29 90; fax: +41-44-632 11 44)
    • Laboratorium für Organische Chemie, Departement Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule, ETH-Zürich, Hönggerberg, HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich (phone: +41-44-632 29 90; fax: +41-44-632 11 44)
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Abstract

Fmoc-β2hSer(tBu)-OH was converted to Fmoc-β2hSec(PMB)-OH in five steps. To avoid elimination of HSeR, the selenyl group was introduced in the second last step (Fmoc2hSer(Ts)-OAll→Fmoc-β2hSec(PMB)-OAll). In a similar way, the N-Boc-protected compound was prepared. With the β2hSe-derivatives, 21 β2-amino-acid building blocks with proteinogenic side chains are now available for peptide synthesis.

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