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pH‐Switchable Vesicles from a Serine‐Derived Guanidiniocarbonyl Pyrrole Carboxylate Zwitterion in DMSO
Author(s) -
Rodler Fabian,
Linders Jürgen,
Fenske Tassilo,
Rehm Thomas,
Mayer Christian,
Schmuck Carsten
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003405
Subject(s) - zwitterion , carboxylate , vesicle , chemistry , serine , pyrrole , stereochemistry , biochemistry , organic chemistry , phosphorylation , molecule , membrane
Tightly closed : Zwitterion 1 forms vesicles that have an approximate size of 50 nm in DMSO solution. The vesicles can be opened and closed by the addition of either acid or base, as vesicle formation depends on the protonation state of zwitterion 1 (see picture). The membrane permeability of the vesicles is surprisingly low: the encapsulated solvent does not exchange with the surrounding solution, even on a time scale of a few hundred milliseconds.