Sequence-Controlled High Molecular Weight Glyco(oligoamide)–PEG
Multiblock Copolymers as Ligands and Inhibitors in Lectin Binding
Version 2 2018-07-18, 18:50
Version 1 2018-07-18, 18:48
Posted on 2018-07-18 - 18:50
A synthesis
toward sequence-controlled multiblock glycopolymers,
presenting a mannopyranoside (Man) glyco(oligoamide) block followed
by a poly(ethylene glycol) (PEG) (M̅n of 6 kDa) block, is shown. Therefore, monodisperse and sequence-defined
glyco(oligoamide) macromonomers derived from solid phase synthesis
(SPS) are polymerized with dithiol-functionalized PEG via thiol–ene
coupling (TEC) in a step-growth fashion. For the polymerization, a
novel building block introducing a norbornene moiety is developed
which is used for end-functionalization of the glyco(oligoamide) macromonomers.
As a highly reactive alkene moiety in photoinduced TEC, this gives
access to X̅n of up to 45. A total
of 12 glyco(oligoamide)–PEG multiblock copolymers with maximum M̅n of 200 kDa are obtained and subjected
to a series of purification steps decreasing overall dispersity. In
different binding studies toward model lectin Concanavalin A, despite
their high number of Man ligands, we see rather weak binding of glycopolymers
that we attribute to the introduction of higher molecular weight PEG
blocks.
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Gerke, Christoph; Jacobi, Fawad; Goodwin, Laura E.; Pieper, Franziska; Schmidt, Stephan; Hartmann, Laura (2018). Sequence-Controlled High Molecular Weight Glyco(oligoamide)–PEG
Multiblock Copolymers as Ligands and Inhibitors in Lectin Binding. ACS Publications. Collection. https://doi.org/10.1021/acs.macromol.8b00982
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AUTHORS (6)
CG
Christoph Gerke
FJ
Fawad Jacobi
LG
Laura E. Goodwin
FP
Franziska Pieper
SS
Stephan Schmidt
LH
Laura Hartmann
KEYWORDS
Man ligandsLectin BindingSPSphotoinduced TECweight PEG blocksnorbornene moietypurification steps6 kDamacromonomersequence-controlled multiblock glycopolymersphase synthesis200 kDastep-growth fashionreactive alkene moietymodel lectin Concanavalinnovel building blockdithiol-functionalized PEGbinding studies