A xyloside is a type of glycoside derived from the sugar xylose.

Proteoglycan (PG) synthesis is initiated by the transfer of D-xylose from UDP-xylose to a serine residue in core proteins. This natural primer acts as a template for the assembly of heparin sulfate, heparin, chondroitin sulfate, and dermatan sulfate side chains, depending on the tissue. However, in 1973 it was determined that synthetic B-D-xylosides can prime glycosaminoglycan (GAG) synthesis by substituting for the core xylosylated protein.

Many Beta-D-xylosides have been studied for use as xylose primes with varying results.[1]

  1. Priming requires the Beta-anomer of xylose.[2]
  2. Priming activity correlates with the activity of the aglycone (cite).
  3. The most active xyloside primers contain O or S in glycosidic linkage.[3]
  4. Priming is dose dependent.[4][5]
  5. Beta-D-xylosides prime GAGs in most cells.
  6. Most of the material created from Beta-D-xylosides priming is excreted into the growth media.
  7. Beta-D-xylosides prime chondroitin sulfate or dermatan sulfate whereas priming of heparin sulfate poorly, except with the appropriate aglycones.[5][6]

Beta-D-xylosides consist of a xylose in beta linkage to an aglycone. The aglycone often consists of a hydrophobic compound which aids in carrying the sugar moiety to the golgi membrane where GAG synthesis takes place.

List of xylosides

  • 2-naphthol-B-D-xyloside

References

  1. ↑ Esko and Montgomery 1995
  2. ↑ Galligani et al. 1975
  3. ↑ Sobue et al. 1987
  4. ↑ Esko et al. 1987
  5. 1 2 Lugemwa and Esko 1991
  6. ↑ Fritz et al., 1994
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