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Applied Biochemistry and Biotechnology

, Volume 42, Issue 2–3, pp 127–135 | Cite as

Covalent attachment of poly(ethyleneglycol) to peptides and proteins

Reevaluation of the synthesis, properties, and usefulness of carbonylimidazol-1-yl-methoxypoly(ethyleneglycol)
  • Jeanne Brygier
  • Michel Gelbcke
  • Claude Guermant
  • Michelle Nijs
  • Danielle Baeyens-Volant
  • Yvan Looze
Article

Abstract

Carbonylimidazol-l-yl-mPEG is obtained quantitatively by reacting methoxypoly(ethyleneglycol) (mPEG) with 1.1 Eq of N,N′-carbonyldiimidazole in the presence of a stoechiometric amount of 4-dimethyl-aminopyridine used as hypernucleophilic acylation catalyst. Carbonylimidazol-l-yl-mPEG is quite stable in aqueous solutions with half-lives up to 70 h in pHs ranging from 6.0 to 7.0 at 25‡C. From reactivity studies toward amines with various nucleophilic strengths, it is suggested that carbonylimidazol-l-yl-mPEG may be best used to modify α-amino terminal function of proteins selectively or to introduce amino function on PEG chains.

Index Entries

Poly(ethyleneglycol) acylation covalent attachment methoxyPEG carbonylimidazol-1-yl-PEG aminoPEG pegylation 

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Copyright information

© Humana Press Inc. 1993

Authors and Affiliations

  • Jeanne Brygier
    • 1
  • Michel Gelbcke
    • 2
  • Claude Guermant
    • 1
  • Michelle Nijs
    • 1
  • Danielle Baeyens-Volant
    • 1
  • Yvan Looze
    • 1
  1. 1.Protein Chemistry Unit, Faculty of MedicineUniversity of BrusselsBrussels
  2. 2.Department of Pharmaceutical Organic Chemistry, Institute of PharmacyUniversity of BrusselsBrussels

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