Automated Synthesis of Chondroitin Sulfate Oligosaccharides

• Chien-Fu Liang^a
• Heung Sik Hahm^a,b
• Narayana Murthy Sabbavarapu
• Peter H. Seeberger

• ^aDepartment of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam, Germany
• ^bDepartment of Chemistry and Biochemistry, Freie Universität Berlin, Berlin, Germany

Glycosaminoglycans (GAGs) are important sulfated carbohydrates prevalently found in the extracellular matrix that serve many biological functions. The synthesis of structurally diverse but defined GAGs is extremely challenging as one has to account for the various sulfation patterns. Described is the automated synthesis of chondroitin sulfate hexasaccharides on a solid support equipped with a photolabile linker. The linker cleavage from the resin is performed in a continuous-flow photoreactor under chemically mild conditions. This approach serves as a general scheme to access oligosaccharides of all GAG families.

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