De novo synthesis of differentially protected L-iduronic acid glycosylating agents.
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.
Bindschädler
Pascal
P
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.
Adibekian
Alexander
A
Grünstein
Dan
D
Seeberger
Peter H
PH
D006031:Glycosylation; D007067:Iduronic Acid / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007067:Iduronic Acid