Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

T.S. Kärkkäinen, K.P. Ravindranathan Kartha, D. MacMillan, R.A. Field

Research output: Contribution to journalArticlepeer-review

Abstract

The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding α-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac3GalNAc-α-Ser)3-Gly and (Ac3GalNAc-α-Thr)3-Gly in 27% and 49% overall yield, respectively. © 2008 Elsevier Ltd. All rights reserved.
Original languageUndefined
Pages (from-to)1830-1834
Number of pages5
JournalCarbohydrate Research
DOIs
Publication statusPublished - 2008

Keywords

  • Antigens
  • Vaccines
  • Tumor cells

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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