Chapter 3. The Chemistry of Sialic Acid

Summary

• Introduction

• Chemical and Enzymatic Synthesis of Sialic Acids

• Chemical Glycosidation of Sialic Acids

  • Direct Chemical Sialylations

    • 2-Chloro Derivatives as Glycosyl Donors

    • 2-Thio Derivatives as Glycosyl Donors

    • 2-Xanthates as Glycosyl Donors

    • 2-Phosphites as Glycosyl Donors

    • Miscellaneous Direct Chemical Methods

  • Indirect Chemical Methods with the Use of a Participating Auxiliary at C-3

    • 3-Bromo- and other 3-O-Auxiliaries

    • 3-Thio and 3-Seleno Auxiliaries

  • Synthesis of (2→8)-Linked Sialosides

• Enzymatic Glycosidations of Sialic Acids

  • Sialyltransferases

    • Metabolic Engineering of the Sialic Acid Biosynthetic Pathway

  • Sialidases

• Synthesis of C- and S-Glycosides of Sialic Acid

• Modifications at N-5

• References