期刊
BIOCONJUGATE CHEMISTRY
卷 21, 期 2, 页码 248-254出版社
AMER CHEMICAL SOC
DOI: 10.1021/bc900253p
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资金
- Core Research for Evolutional Science and Technology (CREST)
- Japan Science and Technology Agency (JST)
Versatile route for click chemistry compatible heterobifunctional PEGS was established through preparation of alpha-tetrahydropyranyloxy-omega-hydroxyl poly(ethylene glycol) (THP-PEG-OH) via ring-opening polymerization of ethylene oxide using 2-(tetrahydro-2H-pyran-2-yloxy)ethanol as an initiator, followed by the functionalization of omega-OH group to either the azido or alkyne group. Quantitative azidation of THP-PEG-OH was confirmed froth the analysis of molecular functionality of the derivatives. While the conversion efficiency of omega-alkynation was appropriately 70%, the unreacted THP-PEG-OH fraction was successfully removed by ion-exchange chromatography after the carboxylation of the hydroxyl group with succinic anhydride. Then, the protecting group of the alpha-end, THP, was removed in mild acidic media, followed by two- or three-step modification of the resulting alpha-hydroxyl group to primary amino or thiol groups. Consequently, click chemistry compatible heterobifunctional PEG derivatives (X-PEG-Y; X = NH2 and SH, Y =Azide and Alkyne) were synthesized with high efficiency and controlled molecular weight.
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