Synthesis of hyaluronic acid oligomers using chemoselective and one-pot strategies.
An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.
Dinkelaar
Jasper
J
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Gold
Henrik
H
Overkleeft
Herman S
HS
Codée
Jeroen D C
JD
van der Marel
Gijsbert A
GA
D005944:Glucosamine / Q000737:chemistry; D006820:Hyaluronic Acid / Q000138:chemical synthesis*; D011108:Polymers / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry
D011108:Polymers; D013865:Thioglycosides; D006820:Hyaluronic Acid; D005944:Glucosamine