Glycoinsulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar-lowering activity

Masaaki Sato, Tetsuya Furuike, Reiko Sadamoto, Naoki Fujitani, Taku Nakahara, Kenichi Niikura, Kenji Monde, Hirosato Kondo, Shin Ichiro Nishimura

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Abstract

Mono-, di-, and trisialyloligosaccharides were introduced to mutant insulins through enzymatic reactions. Sugar chains were sialylated by α2,6-sialyltransferase (α2,6-SiaT) via an accessible glutamine residue at the N-terminus of the B-chain attached by transglutaminase (TGase). Sia2,6-di-LacNAc-Ins(B-F1Q) and Sia2,6-tri-LacNAc-Ins(B-F1Q), displaying two and three sialyl-N-acetyllactosamines, respectively, were administered to hyperglycemic mice. Both branched glycoinsulins showed prolonged glucose-lowering effects compared to native or lactose-carrying insulins, showing that sialic acid is important in obtaining a prolonged effect. Sia2,6-tri-LacNAc-Ins(B-F1Q), in particular, induced a significant delay in the recovery of glucose levels.

Original languageEnglish
Pages (from-to)14013-14022
Number of pages10
JournalJournal of the American Chemical Society
Volume126
Issue number43
DOIs
Publication statusPublished - Nov 3 2004

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Sato, M., Furuike, T., Sadamoto, R., Fujitani, N., Nakahara, T., Niikura, K., Monde, K., Kondo, H., & Nishimura, S. I. (2004). Glycoinsulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar-lowering activity. Journal of the American Chemical Society, 126(43), 14013-14022. https://doi.org/10.1021/ja046426l