Method for the preparation of high molecular weight oligo(alkylene glycol) functionalized polyisocyanopeptides
The present invention relates to a process for the preparation of oligo(alkylene glycol) functionalized polyisocyanopeptides comprising the steps of functionalizing an isocyanopeptide with oligo-(alkylene glycol) side chains and subsequently polymerizing the oligo-alkylene glycol functionalized isocyanopeptides. Several isocyanopeptide may be functionalized with various linear or non-linear oligo-(alkylene glycol) side chains having variable chain length. The alkylene glycol may be selected from the group consisting of ethylene-, propylene-, butylene- or pentylene glycol. Preferably the isocyanopeptides are functionalized with at least 3 ethylene glycol side chains. The peptides may comprise L aminoacids, D-aminoacids or D, L-aminoacids. The obtained oligoalkylene functionalized polyisocyanopeptides are a new class of materials with unique thermo-responsive properties.
1. A method for preparing an oligo(alkylene glycol) functionalized polyisocyanopeptide, the method comprising:
functionalizing an isocyanopeptide with oligo-(alkylene glycol) side chains; and
polymerizing the oligo-alkylene glycol functionalized isocyanopeptides;
wherein the functionalization and/or polymerization step is performed in the presence of an apolar solvent.
2. The method according to claim 1 , wherein the isocyanopeptide is an isocyanodipeptide.
3. The method according to claim 1 , wherein several isocyanopeptides are functionalized with different oligo-(alkylene glycol) side chains having a variable chain length.
4. The method according to claim 1 , wherein the alkylene glycol is selected from the group consisting of ethylene-glycol, propylene-glycol, butylene-glycol and pentylene glycol.
5. The method according to claim 4 , wherein the alkylene glycol is ethylene glycol.
6. The method according to claim 5 , wherein the isocyanopeptide is functionalized with at least 3 ethylene glycol side chains.
7. The method according to claim 1 , wherein the isocyanopeptide monomer comprises D-, L-, and/or D,L-amino acids.
8. The method according to claim 1 , further comprising utilizing a catalyst comprising nickel.
9. A method for preparing an oligo(alkylene glycol) functionalized polyisocyanopeptide, the method comprising:
functionalizing an isocyanopeptide with oligo-(alkylene glycol) side chains; and
polymerizing the oligo-alkylene glycol functionalized isocyanopeptides;
wherein the functionalization and/or polymerization step is performed in an apolar solvent.
10. The method according to claim 9 , wherein the isocyanopeptide is an isocyanodipeptide.
11. The method according to claim 9 , wherein several isocyanopeptides are functionalized with different oligo-(alkylene glycol) side chains having a variable chain length.
12. The method according to claim 9 , whereby the alkylene glycol is selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol, and pentylene glycol.
13. The method according to claim 9 , wherein the alkylene glycol is ethylene glycol.
14. The method according to claim 13 , wherein the isocyanopeptide is functionalized with at least 3 ethylene glycol side chains.
15. The method according to claim 9 , wherein the isocyanopeptide monomer comprises D-, L-, and/or D,L-aminoacids.
16. The method according to claim 9 , further comprising utilizing a catalyst comprising nickel.