title: Mannopyranosyl uronic acid donor reactivity.
abstract: The reactivity of a variety of mannopyranosyl uronic acid donors was assessed in a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-β-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-α-(S)-tolyl mannose.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Marthe T C
authors.initials: MT
authors.lastname: Walvoort
authors.forename: Wilbert
authors.initials: W
authors.lastname: de Witte
authors.forename: Jesse
authors.initials: J
authors.lastname: van Dijk
authors.forename: Jasper
authors.initials: J
authors.lastname: Dinkelaar
authors.forename: Gerrit
authors.initials: G
authors.lastname: Lodder
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D006031:Glycosylation; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D014574:Uronic Acids / Q000737:chemistry*
chemical_list: D014574:Uronic Acids; D008358:Mannose