Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: a sialylated antigenic epitope of small-cell lung cancer

Proc Natl Acad Sci U S A. 2003 Feb 4;100(3):797-802. doi: 10.1073/pnas.0337590100. Epub 2003 Jan 27.

Abstract

The total synthesis of the sialic acid-containing antigenic epitope fucose GM(1) (Fuc-GM(1)) by an improved reactivity-based one-pot synthetic strategy is reported. Based on a thioglycoside reactivity database, three saccharide building blocks, 3, 4, and 5, were designed and prepared to incorporate a descending order of reactivity toward thiophilic activation. Using the reactivity-based one-pot synthetic method, the fully protected Fuc-GM(1) glycoside 2 was furnished in a facile manner, which was globally deprotected to give the Fuc-GM(1) glycoside 1. In addition, using the promoter system 1-(benzensulfinyl)piperidinetrifluoromethanesulfonic anhydride, the product yield was improved and the reaction time was reduced in comparison with the N-iodosuccinimidetrifluoromethanesulfonic acid- and dimethyl (thiomethyl) sulfonium trifluoromethanesulfonate-promoted systems.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrate Sequence
  • Carcinoma, Small Cell / immunology
  • Carcinoma, Small Cell / metabolism*
  • Disaccharides
  • Epitopes
  • Fucose / chemistry*
  • Lung Neoplasms / immunology
  • Lung Neoplasms / metabolism*
  • Molecular Sequence Data
  • N-Acetylneuraminic Acid / chemistry*
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry*

Substances

  • Disaccharides
  • Epitopes
  • Oligosaccharides
  • Fucose
  • G(M1)-oligosaccharide
  • N-Acetylneuraminic Acid