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GRGDS-Functionalized Poly(lactide)-graft-poly(ethylene glycol) Copolymers: Combining Thiol-Ene Chemistry with Staudinger Ligation.

ABSTRACT: A tri(ethylene glycol)-containing lactide analogue was synthesized via thiol-ene chemistry between a bi-functional triethylene glycol and allyl lactide. Subsequent tin-octoate-catalyzed ring-opening polymerization yielded well-defined poly(lactide)-graft-poly(ethylene glycol) copolymers with molecular weights of 6000 g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the copolymers contain azide termini that are capable of 'click'-type postpolymerization functionalization. The utility of this strategy was demonstrated via successful Staudinger ligation to install the Gly-Arg-Gly-Asp-Ser (GRGDS) peptide.

SUBMITTER: Borchmann DE

PROVIDER: S-EPMC3713803 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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GRGDS-Functionalized Poly(lactide)-graft-poly(ethylene glycol) Copolymers: Combining Thiol-Ene Chemistry with Staudinger Ligation.

Borchmann Dorothee E DE Brummelhuis Niels Ten NT Weck Marcus M

Macromolecules 20130601 11

A tri(ethylene glycol)-containing lactide analogue was synthesized via thiol-ene chemistry between a bi-functional triethylene glycol and allyl lactide. Subsequent tin-octoate-catalyzed ring-opening polymerization yielded well-defined poly(lactide)-<i>graft</i>-poly(ethylene glycol) copolymers with molecular weights of 6000 g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the copolymers contain azide termini that are capable of 'click'-type postpolymerization functi ...[more]

PMID: 23878406

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