Synthesis of Selective Inhibitors of Heparan Sulfate and Chondroitin Sulfate Proteoglycan Biosynthesis

  • Caitlin Mencio
  • Dinesh R. Garud
  • Balagurunathan Kuberan
  • Mamoru KoketsuEmail author
Part of the Methods in Molecular Biology book series (MIMB, volume 1229)


Glycosaminoglycan (GAG) side chains of proteoglycans are involved in a wide variety of developmental and pathophysiological functions. Similar to a gene knockout, the ability to inhibit GAG biosynthesis would allow us to examine the function of endogenous GAG chains. However, ubiquitously and irreversibly knocking out all GAG biosynthesis would cause multiple effects making it difficult to attribute a specific biological role to a specific GAG structure in spatiotemporal manner. Reversible and selective inhibition of GAG biosynthesis would allow us to examine the importance of endogenous GAGs to specific cellular, tissue, or organ systems. In this chapter, we describe the chemical synthesis and biological evaluation of 4-deoxy-4-fluoro-xylosides as selective inhibitors of heparan sulfate and chondroitin/dermatan sulfate proteoglycan biosynthesis.

Key words

Glycosaminoglycan biosynthesis 4-Deoxy-4-fluoro-xylosides Proteoglycan inhibitors Heparan sulfate Chondroitin sulfate Dermatan sulfate 



This work was supported in part by NIH grants (GM075168 and HL107152 to B.K.), Human Frontier Science Program grant (RGP0044/2006 to B.K.), and KAKENHI grant (No. 23590005 to M.K.).


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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Caitlin Mencio
    • 1
  • Dinesh R. Garud
    • 2
  • Balagurunathan Kuberan
    • 1
    • 3
    • 4
  • Mamoru Koketsu
    • 5
    Email author
  1. 1.Interdepartmental Program in NeuroscienceUniversity of UtahSalt lake CityUSA
  2. 2.Department of ChemistrySir Parashurambhau CollegePuneIndia
  3. 3.Department of Medicinal ChemistryUniversity of UtahSalt lake CityUSA
  4. 4.Department of BioengineeringUniversity of UtahSalt lake CityUSA
  5. 5.Department of Chemistry and Biomolecular Science, Faculty of EngineeringGifu UniversityGifuJapan

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