On-resin click-glycoconjugation of peptoids

Anna S. Norgren, Carsten Budke, Zs. Majer, Carolin Heggemann, Thomas Koop, Norbert Sewald

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Peptoids are unnatural peptide-like oligomers having the side-chain attached to the glycine nitrogen. In order to investigate how such oligomers are affected upon glycoconjugation, a series of glycosylated peptoids has been synthesized. The conjugation between glycosyl residue and peptoid was achieved by azide + alkyne [3+2] cycloaddition (click reaction). The glycosylated peptoids were obtained by either stepwise assembly from sarcosine and gly-cosylated monomers or global on-resin click glycoconjugation. CD spectroscopic studies were performed on both unglycosylated and glycosylated peptoids with varying chain-length, revealing length and substituent dependences. Additionally, three peptoids were tested for antifreeze activity.

Original languageEnglish
Pages (from-to)488-494
Number of pages7
JournalSynthesis
Issue number3
DOIs
Publication statusPublished - 2009

Fingerprint

Peptoids
Resins
Oligomers
Sarcosine
Alkynes
Azides
Cycloaddition
Chain length
Glycine
Peptides
Amino acids
Nitrogen
Monomers

Keywords

  • Antifreeze testing
  • CD
  • Click chemistry
  • Glycoconjugation
  • Peptoids
  • Triazoles

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Norgren, A. S., Budke, C., Majer, Z., Heggemann, C., Koop, T., & Sewald, N. (2009). On-resin click-glycoconjugation of peptoids. Synthesis, (3), 488-494. https://doi.org/10.1055/s-0028-1083302

On-resin click-glycoconjugation of peptoids. / Norgren, Anna S.; Budke, Carsten; Majer, Zs.; Heggemann, Carolin; Koop, Thomas; Sewald, Norbert.

In: Synthesis, No. 3, 2009, p. 488-494.

Research output: Contribution to journalArticle

Norgren, AS, Budke, C, Majer, Z, Heggemann, C, Koop, T & Sewald, N 2009, 'On-resin click-glycoconjugation of peptoids', Synthesis, no. 3, pp. 488-494. https://doi.org/10.1055/s-0028-1083302
Norgren AS, Budke C, Majer Z, Heggemann C, Koop T, Sewald N. On-resin click-glycoconjugation of peptoids. Synthesis. 2009;(3):488-494. https://doi.org/10.1055/s-0028-1083302
Norgren, Anna S. ; Budke, Carsten ; Majer, Zs. ; Heggemann, Carolin ; Koop, Thomas ; Sewald, Norbert. / On-resin click-glycoconjugation of peptoids. In: Synthesis. 2009 ; No. 3. pp. 488-494.
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