Ways of selective polycondensation of L‐lysine towards linear α‐ and ε‐poly‐L‐lysine |
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| Authors: | Chau Hon Ho Erich Odermatt Ingo Berndt Joerg C Tiller |
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| Institution: | 1. Department of Chemistry, Freiburg Materials Research Center and Institute for Macromolecular Chemistry, Albert‐Ludwigs‐Universitaet Freiburg, Stefan‐Meier‐Str. 21, D‐79104 Freiburg, Germany;2. Aesculap AG & Co. KG, Am Aesculap‐Platz, D‐78532 Tuttlingen, Germany;3. Department of Bio‐ and Chemical Engineering, TU Dortmund, Emil‐Figge‐Str. 66, D‐44227 Dortmund, Germany |
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| Abstract: | 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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| Keywords: | biopolymers polycondensation polylysine |
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