FENG, Xiaoshuang; TATON, Daniel; CHAIKOF, Elliot L.; GNANOU, Yves

doi:10.1021/bm070146r

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FENG, Xiaoshuang
Laboratoire de Chimie des polymères organiques [LCPO]

TATON, Daniel

Laboratoire de Chimie des polymères organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering

CHAIKOF, Elliot L.
Lab Biomol Mat Res [LBMR]

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Biomacromolecules. 2007, vol. 8, n° 8, p. 2374-2378

American Chemical Society

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Doubly functionalized dendrimerlike poly(ethylene oxide)s (PEOs) carrying 16 hydroxyl groups at their periphery and one aldehyde group at their focal point were synthesized up to the fourth generation through an iterative divergent approach. First, a protected aldehyde dihydroxyl compound, namely, 3,3-diethoxy-1,2-propanediol, was used as initiator for the anionic ring-opening polymerization (AROP) of ethylene oxide after partial deprotonation (30%) in dimethyl sulfoxide. The two hydroxyls carried by the PEO chain ends of the first generation were subsequently derivatized so as to generate four hydroxyls via a two-step reaction (allylation and osmylation). The next generations of such dendrimerlike PEOs were grown upon repeating the same cycle of AROP and chain-end modification. At the completion of these reactions, the acetal group present at the core was deprotected under acidic conditions to afford the targeted dendrimerlike PEO of fourth generation with a central aldehyde group. The reactivity and accessibility of the latter function was demonstrated upon its conjugation with aniline used as a model compound.< Leer menos

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METHODOLOGY

STARS

CHEMISTRY

PEGYLATION

ANIONIC-POLYMERIZATION

DRUG-DELIVERY

POLYMERS

DIEPOXIDES

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Bouquet-type dendrimerlike poly(ethylene oxide)s with a focal aldehyde and peripheral hydroxyls

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