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  • Hydrazinopeptide Motifs Synthesized via the Ugi Reaction: An Insight into the Secondary Structure

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    Author(s)
    Krasavin, Mikhail
    Bushkova, Ekaterina
    Parchinsky, Vladislav
    Shumsky, Alexei
    Griffith University Author(s)
    Krasavin, Mikhail
    Year published
    2010
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    Abstract
    A number of Na-alkyl,N߭acylhydrazines have been synthesized via the Ugi reaction of N-acylhydrazones with an isocyanide and trifluoroacetic acid. The trifluoroacetic acid acted as a 'silent partner' and becomes removed upon basic workup of the reaction. These compounds have been efficiently modified further via reductive alkylation to produce Na,Na-dialkyl,N߭acylhydrazines. The two groups of novel hydrazinopeptide motifs have been shown by simple 鈠NMR spectroscopic experiments to display two different secondary structure patterns. These observations were confirmed by X-ray crystallographic analysis. Combining the hydrazone ...
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    A number of Na-alkyl,N߭acylhydrazines have been synthesized via the Ugi reaction of N-acylhydrazones with an isocyanide and trifluoroacetic acid. The trifluoroacetic acid acted as a 'silent partner' and becomes removed upon basic workup of the reaction. These compounds have been efficiently modified further via reductive alkylation to produce Na,Na-dialkyl,N߭acylhydrazines. The two groups of novel hydrazinopeptide motifs have been shown by simple 鈠NMR spectroscopic experiments to display two different secondary structure patterns. These observations were confirmed by X-ray crystallographic analysis. Combining the hydrazone and carboxylic acid moieties in one reaction precursor offers the opportunity for an 'intramolecular' hydrazino-Ugi reaction, which was also demonstrated.
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    Journal Title
    Synthesis
    Volume
    6
    DOI
    https://doi.org/10.1055/s-0029-1219274
    Copyright Statement
    © 2010 Georg Thieme Verlag. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. The definitive version is available at www.thieme-connect.com
    Subject
    Organic Chemical Synthesis
    Analytical Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/48042
    Collection
    • Journal articles

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