Facile solid-phase synthesis of an antifreeze glycoprotein

Ping Hui Tseng, Weir Torn Jiaang, Meng Yang Chang, Shui Tein Chen

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

The antifreeze glycoproteins (AFGPs) 1 are composed of a repeating tripeptide unit (Ala-Thr-Ala) in which the threonine residue is glycosylated with the disaccharide β-D-Gal-(1 → 3)-α-D-GalNAc. A new procedure for synthesizing AFGPs using Fmoc-(Ac4-β-D-Gal-(1 → 3)-benzylidene-α-D-GalNAc)Thr-OH (10) as a building block has been developed. Total synthesis of the AFGPs (n=4, 8) in overall yields of 61% and 33%, respectively, has demonstrated the usefulness of the method. The synthetic AFGPs 1 (n=4, 8) showed a similar conformation to the native AFGPs in their circular dichroism spectra.

Original languageEnglish
Pages (from-to)585-590
Number of pages6
JournalChemistry - A European Journal
Volume7
Issue number3
DOIs
StatePublished - 2 Feb 2001

Keywords

  • Antifreeze
  • Glycoproteins
  • Peptides
  • Solid-phase synthesis
  • T antigen

Fingerprint

Dive into the research topics of 'Facile solid-phase synthesis of an antifreeze glycoprotein'. Together they form a unique fingerprint.

Cite this