# Xyloside

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A **xyloside** is a type of [glycoside](/source/Glycoside) derived from the sugar [xylose](/source/Xylose).

[Proteoglycan](/source/Proteoglycan) (PG) synthesis is initiated by the transfer of [D-xylose](/source/D-xylose) from [UDP-xylose](/source/UDP-xylose) to a [serine](/source/Serine) residue in core proteins. This natural primer acts as a template for the assembly of [heparin sulfate](/source/Heparin_sulfate), [heparin](/source/Heparin), [chondroitin sulfate](/source/Chondroitin_sulfate), and [dermatan sulfate](/source/Dermatan_sulfate) side chains, depending on the tissue. However, in 1973 it was determined that synthetic B-D-xylosides can prime [glycosaminoglycan](/source/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]
1. Priming activity correlates with the activity of the aglycone (cite).
1. The most active xyloside primers contain O or S in glycosidic linkage.[3]
1. Priming is dose dependent.[4][5]
1. Beta-D-xylosides prime GAGs in most cells.
1. Most of the material created from Beta-D-xylosides priming is excreted into the growth media.
1. 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](/source/Golgi_apparatus) where GAG synthesis takes place.

## List of xylosides

- [2-naphthol-B-D-xyloside](/source/2-naphthol-B-D-xyloside)

## References

1. Esko and Montgomery 1995

1. Galligani et al. 1975

1. Sobue et al. 1987

1. Esko et al. 1987

1. Lugemwa and Esko 1991

1. 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](http://jb.oxfordjournals.org/cgi/reprint/74/5/1069))[dead link]

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Adapted from the Wikipedia article [Xyloside](https://en.wikipedia.org/wiki/Xyloside) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Xyloside?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.