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]

Priming requires the Beta-anomer of xylose.^[2]
Priming activity correlates with the activity of the aglycone (cite).
The most active xyloside primers contain O or S in glycosidic linkage.^[3]
Priming is dose dependent.^[4]^[5]
Beta-D-xylosides prime GAGs in most cells.
Most of the material created from Beta-D-xylosides priming is excreted into the growth media.
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

^ Esko and Montgomery 1995
^ Galligani et al. 1975
^ Sobue et al. 1987
^ Esko et al. 1987
^ ^a ^b Lugemwa and Esko 1991
^ 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)^{[permanent dead link‍]}

[1] Esko and Montgomery 1995

[2] Galligani et al. 1975

[3] Sobue et al. 1987

[4] Esko et al. 1987

[LugemwaAndesko-5] Lugemwa and Esko 1991

[6] Fritz et al., 1994

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