Reversible derivatization of sugars with carbobenzyloxy groups and use of the derivatives in solution-phase enzymatic oligosaccharide synthesis

Thomas Norberg*, Elisabet Kallin, Ola Blixt

*Corresponding author for this work

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Abstract

Simple protocols for attaching and detaching carbobenzyloxy (Cbz) groups at the reducing end of sugars was developed. Briefly, lactose was converted into its glycosylamine, which was then acylated with carbobenzyloxy chloride in high overall yield. The obtained lactose Cbz derivative was used in sequential glycosylations using glycosyltransferases and nucleotide sugars in aqueous buffers. Isolation of the reaction products after each step was by simple C-18 solid-phase extraction. The Cbz group was removed by catalytic hydrogenolysis or catalytic transfer hydrogenation followed by in situ glycosylamine hydrolysis. In this way, a trisaccharide (GlcNAc-lactose), a human milk tetrasaccharide (LNnT), and a human milk pentasaccharide (LNFPIII) were prepared in a simple and efficient way.
Original languageEnglish
Article number108272
JournalCarbohydrate Research
Volume502
Number of pages5
ISSN0008-6215
DOIs
Publication statusPublished - 2021

Keywords

  • Derivatization
  • Enzymatic synthesis
  • Milk ogliosaccharides
  • Glycosylamines

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