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Dolichol



 

Dolichol
Identifiers
CAS number 2067-66-5
PubChem 6433320
MeSH Dolichol
Properties
Molecular formula C100H164O
Molar mass 1382.37
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Dolichol refers to any of a group of long-chain mostly unsaturated organic compounds which are made up of varying numbers of isoprene units terminating in an α-saturated isoprenoid group, containing an alcohol functional group.

Additional recommended knowledge

Contents

Functions

Dolichols are adducted to proteins during posttranslational modification. They activate and anchor sugar molecules on cellular membranes.

In addition, they play a role in protein N-glycosylation in the form of dolichol pyrophosphate by carrying the preassembled oligosaccharide Glc3-Man9-GlcNAc2 (where Glc is glucose, Man is mannose, and GlcNAc is N-acetylglucosamine) which is transferred to certain asparagine residues of nascent polypeptide chains. Dolichol is also involved in transfer of the monosaccharides to the forming Glc3-Man9-GlcNAc2-Dolichol carrier.

Role in aging

Dolichol accumulates in tissues over time and has been suggested to be used as a biomarker for aging [1]

Synthesis

It is a product of the HMG-CoA reductase pathway, as characteristic for all terpenes produced via the mevalonate pathway. First, a cis(or Z)-prenyltransferase catalyzes condensation of Farnesyl diphosphate (FPP) with a varying number (dependent on the particular cis-prenyltransferase) of ispentyl diphoshate (IPP) molecules, resulting in polyprenyl diphosphate (also known as dehydrodolichyl diphoshate). This subsequently undergoes loss of both phosphate groups resulting in a polyprenol (dehydrodolichol). Last, the α isoprenoid unit is saturated by α-saturase (still a hypothetical enzyme), and this α-saturated polyprenyl alcohol is Dolichol. [2]

References

  1. ^ "J Gerontol A Biol Sci Med Sci. 2005 Jan;60(1):39-43".
  2. ^ "Schenk, B.; Fernandez, F.; Waechter, C. J. Glycobiology, 2001, 11(5), 61R-70R."
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dolichol". A list of authors is available in Wikipedia.
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