Hiki, Shigehiro ; Kataoka, Kazunori (2007) A facile synthesis of azido-terminated heterobifunctional poly(ethylene glycol)s for “click” conjugation Bioconjugate Chemistry, 18 (6). pp. 2191-2196. ISSN 1043-1802
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Official URL: http://pubs.acs.org/doi/abs/10.1021/bc700152j
Related URL: http://dx.doi.org/10.1021/bc700152j
Abstract
New azido-terminated heterobifunctional poly(ethylene glycol) (PEG) derivatives having primary amine and carboxyl end groups, (Azide-PEG-NH2 and Azide-PEG-COOH, respectively) were synthesized with high efficiency. An α-allyl-ω-hydroxyl PEG was prepared as the first step to Azide-PEG-X (X = NH2 and COOH) through the ring-opening polymerization of ethylene oxide (EO) with allyl alcohol as an initiator, followed by two-step modification of the hydroxyl end to an azido group. To introduce primary amino or carboxyl functional groups, amination and carboxylation reactions of the allyl terminal ends was then conducted by a radical addition of thiol compounds. Molecular functionalities of both ends of the PEG derivatives thus prepared were characterized by 1H, 13C NMR, and MALDI-TOF MS spectra, validating that the reaction proceeded quantitatively. The terminal azido functionality is available to conjugate various ligands with an alkyne group through the 1,3-dipolar cycloaddition reaction condition (“click chemistry”).
Item Type: | Article |
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Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 106178 |
Deposited On: | 01 Feb 2018 16:46 |
Last Modified: | 01 Feb 2018 16:46 |
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