The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates

Carbohydr Res. 2008 Aug 11;343(12):2057-66. doi: 10.1016/j.carres.2008.02.022. Epub 2008 Mar 2.

Abstract

The Amadori rearrangement was introduced as a key step for the conjugation of carbohydrate moieties with suitable amines such as aliphatic amines and amino acid derivatives. The rearrangement products were further transformed into the corresponding 1-N,2-O cyclic carbamates employing triphosgene to obtain anomerically stable glycoconjugates. The reaction conditions were probed on a model substrate, 3,5-di-O-benzyl-alpha,beta-d-glucofuranose and further applied to d-glycero-d-gulo-heptose, which gave 'd-gluco-conjugates' in the alpha-anomeric form exclusively in high isolated yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycoconjugates / chemical synthesis*

Substances

  • Glycoconjugates