Dolichol: A Naturally-Occurring C100 Isoprenoid Alcohol

Abstract

region 190-210 mjA was determined by Dr C. von Planta (Hoffmann-La Roche and Co., Basle) using a vacuum grating spectrometer as described by Planta (1962). Infrared-absorption spectra were recorded by a Perkin-Elmer Infracord (model 137) spectrometer. The highresolution spectra were obtained by Dr C. H. Steele of the Thornton Research Laboratories, Shell, Ellesmere Port, Cheshire, with a Grubb-Parsons double-beam grating spectrometer (model GS 2). Samples were examined as films between NaCl plates whenever possible. Materials of high melting point were studied as KBr disks.

The biological role of dolichol

“…All dolichols so far investigated are in the S-form, and probably only the trans-trans-polycis compound is present in biological membranes, again in contrast with ubiquinone, which is in the all-trans form [15][16][17].…”

“…A family of longer dolichols with [15][16][17][18][19][20][21][22][23] isoprene residues is present, in contrast with ubiquinone, which has only one major form in each individual species (nine isoprene residues in rat; ten in human).…”

Conservation of the PTEN catalytic motif in the bacterial undecaprenyl pyrophosphate phosphatase, BacA/UppP

“…Dolichol, a polyisoprenoid alcohol, was first isolated from pig liver, and is one of the largest lipids in eukaryotes and archaea (Burgos et al, 1963;Pennock et al, 1960). Named for the Greek word for long, dolichos, it can contain 14-24 isoprene units depending on the organism.…”

The effect of dolichol phosphate on the synthesis of lipid bound sugars in embryonic chick brain

“…Dolichol was isolated from pig liver by the method of Burgos et al [2]. Preparative thin-layer chromatography [3] was carried out developing first with chloroform and then eluting the dolichol band, which fluoresced when sprayed with Rhodamine G and gave a green-yellow colour when detected with anisaldehyde [3].…”

“…Polyisoprenols are also present in mammalian tissues [2,31, and their role as acceptors of hexoses from nucleotide sugars has been documented [4-lo]. Leloir and his associates [5, 7, 81 have found that a liver system readily transfers hexoses from sugar nucleotides to dolichol monophosphate.…”