Ways of selective polycondensation of L-lysine towards linear α- and ε-poly-L-lysine
Chau Hon Ho
Department of Chemistry, Freiburg Materials Research Center and Institute for Macromolecular Chemistry, Albert-Ludwigs-Universitaet Freiburg, Stefan-Meier-Str. 21, D-79104 Freiburg, Germany
Search for more papers by this authorErich Odermatt
Aesculap AG & Co. KG, Am Aesculap-Platz, D-78532 Tuttlingen, Germany
Search for more papers by this authorIngo Berndt
Aesculap AG & Co. KG, Am Aesculap-Platz, D-78532 Tuttlingen, Germany
Search for more papers by this authorCorresponding Author
Joerg C. Tiller
Department of Bio- and Chemical Engineering, TU Dortmund, Emil-Figge-Str. 66, D-44227 Dortmund, Germany
Department of Bio- and Chemical Engineering, TU Dortmund, Emil-Figge-Str. 66, D-44227 Dortmund, GermanySearch for more papers by this authorChau Hon Ho
Department of Chemistry, Freiburg Materials Research Center and Institute for Macromolecular Chemistry, Albert-Ludwigs-Universitaet Freiburg, Stefan-Meier-Str. 21, D-79104 Freiburg, Germany
Search for more papers by this authorErich Odermatt
Aesculap AG & Co. KG, Am Aesculap-Platz, D-78532 Tuttlingen, Germany
Search for more papers by this authorIngo Berndt
Aesculap AG & Co. KG, Am Aesculap-Platz, D-78532 Tuttlingen, Germany
Search for more papers by this authorCorresponding Author
Joerg C. Tiller
Department of Bio- and Chemical Engineering, TU Dortmund, Emil-Figge-Str. 66, D-44227 Dortmund, Germany
Department of Bio- and Chemical Engineering, TU Dortmund, Emil-Figge-Str. 66, D-44227 Dortmund, GermanySearch for more papers by this authorAbstract
Polylysines (PL) are highly interesting polymers due to their biocompatibility and their high number of reactive amino groups. So far it was not possible to synthesize them directly from L-lysine. Here, we describe two different synthesis routes to selectively polymerize lysine in one batch without the use of protection groups. Applying 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide as activating agent for the polycondensation of L-lysine in water gave selectively linear ε-PLL. In contrast to this, the polymerization of L-lysine in chloroform in the presence of dicyclohexyl carbodiimide and 18-crown-6 ether selectively afforded pure α-PLL. We also assessed the capability of polylysine derivatization by polymer analog reactions with acetic anhydride, methyl iodide and 2,4,6-trinitrobenzenesulfonic acid. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 5053–5063, 2008
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