Surface PEGylation via native chemical ligation

Eunkyoung Byun, Jangbae Kim, Sung Min Kang, Hyukjin Lee, Duhee Bang, Haeshin Lee

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Native chemical ligation (NCL) is an emerging chemoselective chemistry that forms an amide bond by trans-thioesterification followed by intramolecular nucleophilic rearrangement between thioester and cysteine. The reaction is simple, occurs in a mild aqueous solution, and gives near-quantitative yields of a desired product. Since the first report in 1994, most studies involving the use of NCL have focused on the total synthesis of proteins to address fundamental questions pertaining to many aspects of protein science, such as folding, mirror images, and site-specific labeling of proteins, but applications of the NCL reaction for other areas remain largely unexplored. Herein, we present a facile strategy for surface immobilization of poly(ethylene glycol) (PEG) utilizing the NCL reaction. Surface immobilization of PEG (i.e., PEGylation) plays a key role in preventing nonspecific protein adsorption on surfaces, which is crucial in a wide variety of medical devices. Using cysteine-PEG and thioester-containing phosphonic acid conjugates, we achieved efficient surface PEGylation on titanium surfaces. Ellipsometry, goniometry, and X-ray photoelectron spectroscopy (XPS) unambiguously confirmed the presence of PEGs, which provided nonfouling effects of surfaces. This study indicates that the NCL reaction will be a useful toolkit for surface bioconjugation and functionalization.

Original languageEnglish
Pages (from-to)4-8
Number of pages5
JournalBioconjugate Chemistry
Volume22
Issue number1
DOIs
Publication statusPublished - 2011 Jan 19

Fingerprint

Ligation
Polyethylene glycols
Proteins
Immobilization
Chemical reactions
Cysteine
Photoelectron Spectroscopy
Ethylene Glycol
Titanium
Amides
Adsorption
Ellipsometry
Labeling
Equipment and Supplies
Mirrors
X ray photoelectron spectroscopy
Acids

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

Cite this

Byun, E., Kim, J., Kang, S. M., Lee, H., Bang, D., & Lee, H. (2011). Surface PEGylation via native chemical ligation. Bioconjugate Chemistry, 22(1), 4-8. https://doi.org/10.1021/bc100285p
Byun, Eunkyoung ; Kim, Jangbae ; Kang, Sung Min ; Lee, Hyukjin ; Bang, Duhee ; Lee, Haeshin. / Surface PEGylation via native chemical ligation. In: Bioconjugate Chemistry. 2011 ; Vol. 22, No. 1. pp. 4-8.
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Byun, E, Kim, J, Kang, SM, Lee, H, Bang, D & Lee, H 2011, 'Surface PEGylation via native chemical ligation', Bioconjugate Chemistry, vol. 22, no. 1, pp. 4-8. https://doi.org/10.1021/bc100285p

Surface PEGylation via native chemical ligation. / Byun, Eunkyoung; Kim, Jangbae; Kang, Sung Min; Lee, Hyukjin; Bang, Duhee; Lee, Haeshin.

In: Bioconjugate Chemistry, Vol. 22, No. 1, 19.01.2011, p. 4-8.

Research output: Contribution to journalArticle

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