Chemical Synthesis of Human Milk Oligosaccharides: Lacto- N-hexaose Galβ1→3GlcNAcβ1→3 [Galβ1→4GlcNAcβ1→6] Galβ1→4Glc

J Org Chem. 2019 Dec 20;84(24):16192-16198. doi: 10.1021/acs.joc.9b02701. Epub 2019 Dec 5.

Abstract

The first synthesis of lacto-N-hexaose (LNH) has been completed using a convergent strategy. The donor-acceptor protecting-leaving group combinations were found to be of paramount significance for achieving successful glycosylations and minimizing side reactions. Lacto-N-tetraose, another common human milk oligosaccharide, was also obtained en route to the target LNH.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Humans
  • Milk, Human / chemistry*
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry

Substances

  • Oligosaccharides