Controlled synthesis of phosphorylcholine derivatives of poly(serine) and poly(homoserine)

Journal of the American Chemical Society
Ilya Yakovlev, Timothy J Deming

Abstract

We report methods for the synthesis of polypeptides that are fully functionalized with desirable phosphorylcholine, PC, groups. Because of the inherent challenges in the direct incorporation of the PC group into α-amino acid N-carboxyanhydride (NCA) monomers, we developed a synthetic approach that combined functional NCA polymerization with efficient postpolymerization modification. While poly(L-phosphorylcholine serine) was found to be unstable upon synthesis, we successfully prepared poly(L-phosphorylcholine homoserine) with controlled chain lengths and found these to be water-soluble with disordered chain conformations.

References

Dec 13, 2006·Langmuir : the ACS Journal of Surfaces and Colloids·J-J YuanA L Lewis
Mar 27, 2009·Chemical Communications : Chem Comm·Beth M CooperTodd Emrick
Nov 5, 2010·Biomacromolecules·Jessica R Kramer, Timothy J Deming
May 11, 2011·Biomacromolecules·Sophie MongeJean-Jacques Robin
Dec 1, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Semra Colak, Gregory N Tew
Feb 14, 2013·Cancer Letters·Carla PegoraroGiuseppe Battaglia
Jun 8, 2013·Molecular Pharmaceutics·Samantha McRae PageTodd Emrick
Mar 8, 2014·Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology·Timothy J Deming

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Citations

Jul 7, 2015·Chemical Reviews·Timothy J Deming
Nov 5, 2016·Chemical Reviews·Vincent FroidevauxBernard Boutevin
Sep 18, 2018·Chemical Society Reviews·Greta Becker, Frederik R Wurm
Oct 25, 2017·Polymers·Carmen M González-HenríquezJuan Rodríguez-Hernández

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