Synthesis of iduronic acid building blocks for the modular assembly of glycosaminoglycans.
The modular synthesis of glycosaminoglycans requires straightforward methods for the production of large quantities of protected uronic acid building blocks. In particular, the preparation of fully differentiated iduronic acids has proven particularly challenging. An efficient route to methyl 3-O-benzyl-1,2-O-isopropylidene-alpha-l-idopyranosiduronate 6 from diacetone glucose in nine steps and 36% overall yield is described. Idopyranosiduronate 6 is useful as a glycosyl acceptor and as an intermediate that may be further elaborated into iduronic acid trichloroacetimidate glycosyl donors for the assembly of glycosaminoglycan structures as illustrated here.
Lohman
Gregory J S
GJ
Massachusetts Institute of Technology, 77 Massachusetts Avenue 18-292, Cambridge, Massachusetts 02139, USA.
Hunt
Diana K
DK
Högermeier
Jens A
JA
Seeberger
Peter H
PH
D020650:Combinatorial Chemistry Techniques; D006025:Glycosaminoglycans / Q000138:chemical synthesis*; D006031:Glycosylation; D007067:Iduronic Acid / Q000737:chemistry
D006025:Glycosaminoglycans; D007067:Iduronic Acid