Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 416–429, doi:10.3762/bjoc.14.30

• these materials, in concert with DMC-mediated oxazoline formation as a final step, allow access to a selection of N-glycan oxazoline structures both in larger quantities and in a more expedient fashion than is achievable by total synthesis. Keywords: DMC, ENGase; glycosyl oxazolines; N-glycans

• ; oligosaccharides; Review Introduction Glycosyl oxazolines are high-energy intermediates on the hydrolytic pathway of some [1][2][3][4][5] (but not all) [6] of the numerous glycosidases that hydrolyse linkages between 2-acetamido sugars and other species. In particular the endo-β-N-acetylglucosaminidases [7

• intermediate [8]. Glycosyl oxazolines first drew the attention of synthetic chemists due to their use as glycosyl donors for the synthesis of oligosaccharides that comprise 2-amino-2-dexoy sugars [9]. Though the majority of synthetic work focussed on production and reaction of gluco-configured oxazolines (i.e