Xyloside

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

• 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. 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)