From polymer to size-defined oligomers: a highly divergent and stereocontrolled construction of chondroitin sulfate A, C, D, E, K, L, and M oligomers from a single precursor: part 2.
An efficient, stereocontrolled, and highly divergent approach for the preparation of oligomers of chondroitin sulfate (CS) A, C, D, E, K, L, and M variants, starting from a single precursor easily obtained by semisynthesis from abundant natural polymer is reported for the first time. Common intermediates were designed that allowed the straightforward construction of O-sulfonated species either on the D-galactosamine unit (CS-A, -C, and -E) or on both D-glucuronic acid and D-galactosamine units (CS-D and CS-K, -L, and -M). This strategy represents a successful improvement and brings a definitive answer toward the synthesis of such complex molecules with numerous relevant biological functions.
Jacquinet
Jean-Claude
JC
Institut de Chimie Organique et Analytique, UMR 6005 Université d'Orléans et CNRS, Université d'Orléans, BP 6759, 45067 Orléans Cedex, France. Jean-Claude.Jacquinet@univ-orleans.fr
Lopin-Bon
Chrystel
C
Vibert
Aude
A
D002809:Chondroitin Sulfates / Q000138:chemical synthesis* / Q000737:chemistry; D005688:Galactosamine / Q000737:chemistry; D020723:Glucuronic Acid / Q000737:chemistry; D006031:Glycosylation; D009844:Oligosaccharides / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009844:Oligosaccharides; D011108:Polymers; C065068:chondroitin sulfate D; D005688:Galactosamine; D020723:Glucuronic Acid; D002809:Chondroitin Sulfates