Xyloside

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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 slfate 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[edit]

References[edit]

  1. ^ Esko and Montgomery 1995
  2. ^ Galligani et al. 1975
  3. ^ Sobue et al. 1987
  4. ^ Esko et al. 1987
  5. ^ a b Lugemwa and Esko 1991
  6. ^ Fritz et al., 1994
  • The influence of p-nitrophenyl beta-d-xyloside on the synthesis of proteochondroitin sulfate by slices of embryonic chick cartilage.,Okayama M, Kimata K, Suzuki S.,J Biochem. 1973 Nov;74(5):1069-73. (http://jb.oxfordjournals.org/cgi/reprint/74/5/1069)