Dolichol

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File:Doichol.png
Structure of Dolichol. Infobox below is for 20 isoprene residues.
Template:Chembox E number
Dolichol
Identifiers
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MeSH Dolichol
Properties
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.

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."

External links


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