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Mild and Chemoselective Peptide-Bond Cleavage of Peptides and Proteins at Azido Homoalanine

Authors

  • Jaap Willem Back Dr.,

    1. Swammerdam Insitute for Life Sciences, Mass Spectrometry Group, University of Amsterdam, Nieuwe Achtergracht 166, 1018WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6971
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  • Olivier David Dr.,

    1. Laboratoire de Photochimie et Photophysique Supramoléculaire et Macromoléculaire, École Normale Supérieure de Cachan, 61 Avenue du Président Wilson, 94235 Cachan, France
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  • Gertjan Kramer,

    1. Swammerdam Insitute for Life Sciences, Mass Spectrometry Group, University of Amsterdam, Nieuwe Achtergracht 166, 1018WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6971
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  • Géraldine Masson Dr.,

    1. van't Hoff Institute for Molecular Sciences, Department of Organic Cchemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018WS Amsterdam, The Netherlands
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  • Piotr T. Kasper,

    1. Swammerdam Insitute for Life Sciences, Mass Spectrometry Group, University of Amsterdam, Nieuwe Achtergracht 166, 1018WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6971
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  • Leo J. de Koning Dr.,

    1. Swammerdam Insitute for Life Sciences, Mass Spectrometry Group, University of Amsterdam, Nieuwe Achtergracht 166, 1018WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6971
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  • Luitzen de Jong Dr.,

    1. Swammerdam Insitute for Life Sciences, Mass Spectrometry Group, University of Amsterdam, Nieuwe Achtergracht 166, 1018WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6971
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  • Jan H. van Maarseveen Dr.,

    1. van't Hoff Institute for Molecular Sciences, Department of Organic Cchemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018WS Amsterdam, The Netherlands
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  • Chris G. de Koster Prof. Dr.

    1. Swammerdam Insitute for Life Sciences, Mass Spectrometry Group, University of Amsterdam, Nieuwe Achtergracht 166, 1018WV Amsterdam, The Netherlands, Fax: (+31) 20-525-6971
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  • We gratefully acknowledge Dr. Michael van der Horst for the pHISP plasmid and assistance with cloning and purification of PYP and the Yale E.coli genetic stock center for providing E. coli strain CAG18491. This research was supported by a Horizon Breakthrough grant to J.W.B. from The Nationaal Regie Orgaan Genomics (NROG) of the Netherlands Organization for Scientific Research (NWO). The ESI-FTMS, MALDI-TOF, and QTOF mass spectrometers were largely funded by NWO-CW and NWO-MW.

Abstract

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Ein sanfter Bruch: Peptide, die die nichtnatürliche, aber proteogene Aminosäure Azidohomoalanin enthalten, lassen sich durch Phosphan- oder Dithiol-vermittelte reduktive Aktivierung der Azidfunktionalität in wässrigen Puffern spalten (siehe Schema). Das dabei gebildete C-terminale Lacton eines Peptidfragments kann einfach weiter derivatisiert werden.

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