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

Dorothee E. Borchmann, Niels Ten Brummelhuis, Marcus Weck

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)4426-4431
Number of pages6
JournalMacromolecules
Volume46
Issue number11
DOIs
StatePublished - Jun 11 2013

Fingerprint

glycyl-arginyl-glycyl-aspartyl-serine
Ethylene Glycol
Ethylene glycol
Sulfhydryl Compounds
Grafts
Polyethylene glycols
Copolymers
Azides
Tin
Ring opening polymerization
Polydispersity
Glycols
Peptides
Molecular weight
dilactide
poly(lactide)

ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Cite this

GRGDS-functionalized poly(lactide)-graft-poly(ethylene glycol) copolymers : Combining thiol-ene chemistry with Staudinger ligation. / Borchmann, Dorothee E.; Ten Brummelhuis, Niels; Weck, Marcus.

In: Macromolecules, Vol. 46, No. 11, 11.06.2013, p. 4426-4431.

Research output: Contribution to journalArticle

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