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Introduction of Functional Groups into Peptides via N-Alkylation

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    Introduction of Functional Groups into Peptides via N-Alkylation
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    Department Chemie, Lehrstuhl II für organische Chemie, Technische Universität München, Lichtenbergstraβe 4, D-85747 Garching, Germany, and Nuklearmedizinische Klinik and Poliklinik, Klinikum rechts der Isar, Technische Universität München, Ismaninger Straβe 22, D-81675 München, Germany
    [email protected]
    †Department Chemie, Lehrstuhl II für organische Chemie.
    ‡Nuklearmedizinische Klinik and Poliklinik, Klinikum rechts der Isar.
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    Organic Letters

    Cite this: Org. Lett. 2008, 10, 10, 2015–2018
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    https://doi.org/10.1021/ol800654n
    Published April 12, 2008
    Copyright © 2008 American Chemical Society
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    Abstract

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    An optimized protocol for the mild and selective Fukuyama−Mitsunobu reaction was used for mono- and di-N-alkylation on solid support. Thereby, nonfunctionalized aliphatic and aromatic residues are quickly introduced into transiently protected, primary amines of a linear peptide. N-Alkylation can also be used to implement alkyl chains carrying (protected) functionalities suited for subsequent modification. Applicability of this method is demonstrated by various N-alkylated analogues of a cyclic CXCR4 receptor antagonist originally developed by Fujii et. al.

    Copyright © 2008 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2008, 10, 10, 2015–2018
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol800654n
    Published April 12, 2008
    Copyright © 2008 American Chemical Society
    Request reuse permissions

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