Bifunctional bisamphiphilic transmembrane building blocks for artificial signal transduction.

[摘要]：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 alc. was targeted by a bisphosphonate dianion. Signaling units comprised an N-protected cysteine (thiol nucleophile) and an N-protected cysteine/pyridine disulfide, resp. (disulfide substrate). All these polar headgroups were connected to the hydroxy of the lipid core by ester formation.

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