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Synthesis of a new neoglycopeptide for inhibition of lactose permease

Dedicated to professor Fritz Jähnig, who inspired this work

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Summary

A new neoglycopeptide was synthesized and tested for its capability to bind to lactose permease ofEscherichia coli and to inhibit the transport of lactose. The free 5′-carboxypentyl-1-thio-β-d-galactopyranoside or the protected 2,3,4,6-tetra-O-acetyl-5′-carboxypentyl-1-thio-β-d-galactopyranoside was linked to the N-terminal α-amino group of the resin bound heptapeptide H-Phe-Phe-Gly-Gly-Gly-Gly-Ala-OH by different activation methods. Upon cleavage from the resin, deacetylation and purification, a neoglycopeptide which showed a significant inhibition of lactose permease was obtained.

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Author notes

  1. Peter Nollert

    Present address: Biozentrum, University of Basel, Klingelbergstrasse 70, CH-4056, Basel, Switzerland

  2. Karl-Heinz Wiesmüller

    Present address: EVOTEC Biosystems GmbH, Grandweg 64, D-22529, Hamburg, Germany

Authors and Affiliations

  1. Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076, Tübingen, Germany

    Stefan Kienle

  2. Abteilung Membranbiochemie, Max-Planck-Institut für Biologie, Corrensstrasse 38, D-72076, Tübingen, Germany

    Peter Nollert

  3. Naturwissenschaftliches und Medizinisches Institut an der Universität Tübingen, Eberhardstrasse 29, D-72762, Reutlingen, Germany

    Karl-Heinz Wiesmüller

Authors
  1. Stefan Kienle
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  2. Peter Nollert
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  3. Karl-Heinz Wiesmüller
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Corresponding author

Correspondence to Stefan Kienle.

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Kienle, S., Nollert, P. & Wiesmüller, KH. Synthesis of a new neoglycopeptide for inhibition of lactose permease. Lett Pept Sci 6, 143–149 (1999). https://doi.org/10.1007/BF02443629

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  • DOI: https://doi.org/10.1007/BF02443629

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