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Synthesis 2008(14): 2247-2256  
DOI: 10.1055/s-2008-1067155
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Bifunctional Bisamphiphilic Transmembrane Building Blocks for Artificial ­Signal Transduction

Michael Maue, Kai Bernitzki, Manuel Ellermann, Thomas Schrader*
Fachbereich Chemie, Universität Duisburg-Essen, Universitätsstr. 5, 45117 Essen, Germany
Fax: +49(201)1834252; e-Mail: Thomas.Schrader@uni-due.de;
Further Information

Publication History

Received 24 May 2008
Publication Date:
02 July 2008 (online)

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Abstract

A convergent modular total synthesis is described which affords bisamphiphilic bifunctional transmembrane building blocks useful for artificial signal transduction across membranes. The concept relies on direct Glaser-Hay coupling of lithocholic or cholenic acid propargyl esters, carrying recognition or signaling units on their opposite hydroxy functionalities. For catechol recognition, a 2-(aminomethyl)phenylboronic acid was introduced, while the ammonium alcohol was targeted by a bisphosphonate dianion. Signaling units comprised an N-protected cysteine (thiol nucleophile) and an N-protected cysteine/pyridine disulfide, respectively (disulfide substrate). All these polar headgroups were connected to the hydroxy of the lipid core by ester formation.

Key words

signal transduction - phosphonate - Glaser-Hay coupling - disulfide coupling

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