GRGDS-functionalized poly(lactide)-graft-poly(ethylene glycol) copolymers: Combining thiol-ene chemistry with Staudinger ligation

Dorothee E. Borchmann; Niels Ten Brummelhuis; Marcus Weck

doi:10.1021/ma4005633

GRGDS-functionalized poly(lactide)-graft-poly(ethylene glycol) copolymers: Combining thiol-ene chemistry with Staudinger ligation

Dorothee E. Borchmann, Niels Ten Brummelhuis, Marcus Weck

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A tri(ethylene glycol)-containing lactide analogue was synthesized via thiol-ene chemistry between a bifunctional 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 6 × 10³g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the copolymers contain azide termini that are capable of efficient postpolymerization functionalization. The utility of this strategy was demonstrated via successful Staudinger ligation to install the Gly-Arg-Gly-Asp-Ser (GRGDS) peptide.

Original language	English (US)
Pages (from-to)	4426-4431
Number of pages	6
Journal	Macromolecules
Volume	46
Issue number	11
DOIs	https://doi.org/10.1021/ma4005633
State	Published - Jun 11 2013

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/ma4005633

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abstract = "A tri(ethylene glycol)-containing lactide analogue was synthesized via thiol-ene chemistry between a bifunctional 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 6 × 103g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the copolymers contain azide termini that are capable of efficient postpolymerization functionalization. The utility of this strategy was demonstrated via successful Staudinger ligation to install the Gly-Arg-Gly-Asp-Ser (GRGDS) peptide.",

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AU - Weck, Marcus

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AB - A tri(ethylene glycol)-containing lactide analogue was synthesized via thiol-ene chemistry between a bifunctional 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 6 × 103g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the copolymers contain azide termini that are capable of efficient postpolymerization functionalization. The utility of this strategy was demonstrated via successful Staudinger ligation to install the Gly-Arg-Gly-Asp-Ser (GRGDS) peptide.

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GRGDS-functionalized poly(lactide)-graft-poly(ethylene glycol) copolymers: Combining thiol-ene chemistry with Staudinger ligation

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