title: De novo synthesis of differentially protected L-iduronic acid glycosylating agents.
abstract: A divergent de novo synthesis of six differentially protected l-iduronic acid thioglycosides from a common advanced precursor is described. The key step of this synthetic sequence is the stereoselective elongation of dithioacetal protected C5-dialdehyde 11 via a highly diastereoselective MgBr(2).OEt(2)-mediated cyanation. Orthogonally protected l-iduronic acid building blocks obtained by this synthesis are expected to facilitate access to differentially sulfated heparins for microarray-based structure-activity relationship studies.
authors.affiliation: Max Planck Institute for Colloids and Interfaces, Department of Biomolecular Systems, Am Mühlenberg 1, 14476 Potsdam, Germany; Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Pascal
authors.initials: P
authors.lastname: Bindschädler
authors.forename: Alexander
authors.initials: A
authors.lastname: Adibekian
authors.forename: Dan
authors.initials: D
authors.lastname: Grünstein
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D006031:Glycosylation; D007067:Iduronic Acid / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007067:Iduronic Acid