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Induction of Unexpected Left-Handed Helicity by an N-Terminal L-Amino Acid in an Otherwise Achiral Peptide Chain

Authors

  • Robert A. Brown,

    1. School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (United Kingdom)
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  • Dr. Tommaso Marcelli,

    1. School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (United Kingdom)
    2. Dipartimento di Chimica, Materiali e Ingegneria Chimica “Giulio Natta”, Politecnico di Milano via Mancinelli 7, 20131 Milano (Italy)
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  • Dr. Matteo De Poli,

    1. School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (United Kingdom)
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  • Dr. Jordi Solà,

    1. School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (United Kingdom)
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  • Prof. Jonathan Clayden

    Corresponding author
    1. School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (United Kingdom)
    • School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL (United Kingdom)
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  • This work was supported by the BBSRC, EPSRC, and ERC. We are grateful to Prof. Fernando Formaggio, Prof. Claudio Toniolo, Prof. Tadashi Mori, and Dr. Alison Edwards for helpful discussions, and to Dean Holt and Romina Wechsel for synthetic assistance. J.C. is the recipient of a Royal Society Wolfson Research Merit award. T.M. acknowledges the MIUR (Rientro dei Cervelli 2008) and the Politecnico di Milano for financial support. We are indebted to CILEA for the generous allocation of computer time.

Abstract

original image

Peptidhelices aus L-Aminosäuren sind in der Regel rechtsgängig. Eine Ausnahme bilden Peptidhelices, die aus den achiralen Aminosäuren 2-Aminoisobuttersäure und Glycin sowie einer einzelnen chiralen Aminosäure am N-Terminus bestehen. Diese Helices sind linksgängig, wenn am N-Terminus eine tertiäre proteinogene Aminosäure wie L-Valin ist (links im Bild), aber rechtsgängig, wenn am N-Terminus die quartäre Aminosäure L-α-Methylvalin ist (rechts).

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