mz500108n_si_001.pdf (922.36 kB)
Synthesis of an Amphiphilic β‑Turn Mimetic Polymer Conjugate
journal contribution
posted on 2014-04-15, 00:00 authored by Marlen Malke, Haitham Barqawi, Wolfgang H. BinderA new biomimetic polymer containing
a beta-turn mimetic element
(1) was synthesized, using a combination of living carbocationic
polymerization (LCCP), amidation, and “click” chemistry.
Two different α-ω-functionalized polyisobutylenes (PIBs 3 and 5) bearing either an alkyne group (PIB 3) or a primary amine group (PIB 5) were directly
synthesized via LCCP. The linking of the two PIB strands with the
closely positioned carboxyl/azido moieties of a β-turn dipeptide
(BTD) 2 was achieved via a sequence of amidation reaction
and the CuI-mediated azide/alkyne “click”
reaction. By means of size exclusion chromatography (SEC), matrix-assisted
laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF
MS), NMR spectroscopy, and LC/MALDI-TOF MS, a detailed structural
proof of the β-turn mimetic PIB conjugate (1) was
possible.