TY - JOUR
T1 - Accelerated Polypeptide Synthesis via N-Carboxyanhydride Ring Opening Polymerization in Continuous Flow
AU - Vrijsen, Jeroen Hendrik
AU - Rasines Mazo, Alicia
AU - Junkers, Tanja
AU - Qiao, Greg Guanghua
PY - 2020/9/1
Y1 - 2020/9/1
N2 - In nature, polypeptide-based materials are ubiquitous, yet their synthetic production is hampered by high cost, limited scalability, and often stringent reaction conditions. Herein an elegant approach is presented for N-carboxyanhydride ring opening polymerization (NCA ROP) of Nε-benzyloxycarbonyl-l-lysine (ZLL) and γ-benzyl-l-glutamate (BLG) NCA in continuous flow. The polymerization is initiated by primary amine initiators using N,N-dimethylformamide (DMF) as solvent. Carrying out the reaction in a silicon microflow reactor speeds up the rate of ROP (92% conversion in 40 min in flow as opposed to 6 h in batch) due to highly efficient permeation of CO2 through the reactor tubing. The polymerization strategy provides a facile, scale-up friendly alternative to traditional batch mode polymerization and has the capability of streamlining NCA ROP.
AB - In nature, polypeptide-based materials are ubiquitous, yet their synthetic production is hampered by high cost, limited scalability, and often stringent reaction conditions. Herein an elegant approach is presented for N-carboxyanhydride ring opening polymerization (NCA ROP) of Nε-benzyloxycarbonyl-l-lysine (ZLL) and γ-benzyl-l-glutamate (BLG) NCA in continuous flow. The polymerization is initiated by primary amine initiators using N,N-dimethylformamide (DMF) as solvent. Carrying out the reaction in a silicon microflow reactor speeds up the rate of ROP (92% conversion in 40 min in flow as opposed to 6 h in batch) due to highly efficient permeation of CO2 through the reactor tubing. The polymerization strategy provides a facile, scale-up friendly alternative to traditional batch mode polymerization and has the capability of streamlining NCA ROP.
KW - continuous flow chemistry
KW - flow polymerization
KW - N-carboxyanhydride ring opening polymerization
UR - http://www.scopus.com/inward/record.url?scp=85088262637&partnerID=8YFLogxK
U2 - 10.1002/marc.202000071
DO - 10.1002/marc.202000071
M3 - Article
AN - SCOPUS:85088262637
SN - 1022-1336
VL - 41
JO - Macromolecular Rapid Communications
JF - Macromolecular Rapid Communications
IS - 18
M1 - 2000071
ER -