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Issue 8, 2011
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An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation

Samuel B. Pollocka  and  Stephen B.H. Kent*a 
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* Corresponding authors

a Department of Chemistry, Department of Biochemistry and Molecular Biology, Institute for Biophysical Dynamics, The University of Chicago, Chicago, USA
E-mail: skent@uchicago.edu

Abstract

The low reactivity of peptide-prolyl-thioesters in native chemical ligation is not due to steric effects at the β-carbon, but rather to the presence of a carbonyl moiety on the nitrogen atom of the proline.

Graphical abstract: An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation

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Publication details

The article was received on 28 Sep 2010, accepted on 22 Nov 2010 and first published on 21 Dec 2010


Article type: Communication
DOI: 10.1039/C0CC04120C
Citation: Chem. Commun., 2011,47, 2342-2344
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    An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation

    S. B. Pollock and S. B.H. Kent, Chem. Commun., 2011, 47, 2342
    DOI: 10.1039/C0CC04120C

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