Identification and characterization of dolichyl dolichoate, a novel isoprenoic derivative in bovine thyroid

Steen, L.; Dessel, G. Van; Wolf, M.; Lagrou, A.; Hilderson, H. J.; Keukeleire, Denis De; Pinkse, Frans A.; Fokkens, Roel H.; Dierick, W.

doi:10.1016/0005-2760(84)90130-9

Cited by 29 publications

(7 citation statements)

References 15 publications

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“…However, we do not exclude the possibility that dolichol is formed from dehydrodolichal, because in a preliminary study the addition of NADP ϩ to an assay mixture containing NADPH enhanced the activity of dolichol synthesis. Steen et al (22) have reported the identification of dolichyl dolichoate in bovine thyroid. The formation of dehydrodolichal is well understood as being involved in the biosynthesis of the dolichoate.…”

Section: Table III Assays With [4b-3 H]nadph-generating Systemmentioning

confidence: 98%

Enzymatic Formation of Dehydrodolichal and Dolichal, New Products Related to Yeast Dolichol Biosynthesis

Sagami

Igarashi

Tateyama

et al. 1996

Journal of Biological Chemistry

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Two new polyprenyl products in addition to dehydrodolichol and dolichol were detected by two-plate silica gel thin layer chromatography of nonpolar products formed from [1-14C]isopentenyl diphosphate and farnesyl diphosphate in the reaction with a crude 1,000 x g supernatant of yeast homogenates in the presence of NADPH. The new products were indistinguishable from authentic dehydrodolichal and dolichal. Analyses of the time-dependent and pH-dependent formation of the four products including dehydrodolichal and dolichal suggested that the biosynthetic pathway from dehydrodolichol leading to dolichal is different from that to dolichol. In double-labeled experiments with a combination of -l-14C-isopentenyl diphosphate and a [4B-3H]NADPH-generating system, the ratio of 3H- and 14C-derived radioactivities found in dolichal was six times higher than that in dolichol. A small amount of 3H-labeled dehydrodolichol was also detected. Considering the fact that dolichol is synthesized from dehydrodolichol (Sagami, H., Kurisaki, A., and Ogura, K. (1993) J. Biol. Chem. 268, 10109-10113), we propose that dehydrodolichol is a common branch point intermediate in the biosynthetic pathways leading to dolichal and dolichol and that dehydrodolichal is an intermediate in the pathway from dehydrodolichol to dolichal.

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Section: Table III Assays With [4b-3 H]nadph-generating Systemmentioning

confidence: 98%

Enzymatic Formation of Dehydrodolichal and Dolichal, New Products Related to Yeast Dolichol Biosynthesis

Sagami

Igarashi

Tateyama

et al. 1996

Journal of Biological Chemistry

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“…Similarly to the phytol to phytenic/phytanic acid conversion (see "Auxiliary enzymes and proteins related to ␣ -oxidation"), farnesol and geranylgeraniol can be oxidized to 2-enoic/2,3-dihydro acids in mammalian cells ( 52,53 ). Attempts to study the degradation of dolichols are rather limited, although the presence of dolichoic acid was documented several years ago in bovine thyroid ( 54 ) and more recently in the sub- be a nonspecifi c effect of SCP2, well known for its lipid binding properties ( 66 ). The ligand binding cavity of SCP2 can accommodate multiple lipids, including long-chain acyl-CoAs, which are high affi nity ligands.…”

Section: Substrates For ␣ -Oxidationmentioning

confidence: 99%

Biochemistry and genetics of inherited disorders of peroxisomal fatty acid metabolism

Veldhoven

2010

Journal of Lipid Research

284

290

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“…All tissues in eukaryotic organisms contain dolichol metabolites. In human, they occur as dolichol (Dol) or dolichyl-phosphate (Dol-P), while also dolichol esters and dolichoic acid have been identified, for example in bovine thyroid (Steen et al 1984 ; Van Dessel et al 1993 ) and human brain (Guan 2009 ). Apart from the well studied localization of Dol-P in the endoplasmic reticulum for protein N-glycosylation, almost all organelle membranes, such as Golgi, mitochondria and lysosomes, contain dolichol metabolites.…”

Section: Biosynthesis Of Dolicholmentioning

confidence: 99%

Genetic defects in dolichol metabolism

Buczkowska

Świeżewska

Lefeber

2014

J of Inher Metab Disea

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Congenital disorders of glycosylation (CDG) comprise a group of inborn errors of metabolism with abnormal glycosylation of proteins and lipids. Patients with defective protein N-glycosylation are identified in routine metabolic screening via analysis of serum transferrin glycosylation. Defects in the assembly of the dolichol linked Glc3Man9GlcNAc2 glycan and its transfer to proteins lead to the (partial) absence of complete glycans on proteins. These defects are called CDG-I and are located in the endoplasmic reticulum (ER) or cytoplasm. Defects in the subsequent processing of protein bound glycans result in the presence of truncated glycans on proteins. These defects are called CDG-II and the enzymes involved are located mainly in the Golgi apparatus. In recent years, human defects have been identified in dolichol biosynthesis genes within the group of CDG-I patients. This has increased interest in dolichol metabolism, has resulted in specific recognizable clinical symptoms in CDG-I and has offered new mechanistic insights in dolichol biosynthesis. We here review its biosynthetic pathways, the clinical and biochemical phenotypes in dolichol-related CDG defects, up to the formation of dolichyl-P-mannose (Dol-P-Man), and discuss existing evidence of regulatory networks in dolichol metabolism to provide an outlook on therapeutic strategies.

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Identification and characterization of dolichyl dolichoate, a novel isoprenoic derivative in bovine thyroid

Cited by 29 publications

References 15 publications

Enzymatic Formation of Dehydrodolichal and Dolichal, New Products Related to Yeast Dolichol Biosynthesis

Enzymatic Formation of Dehydrodolichal and Dolichal, New Products Related to Yeast Dolichol Biosynthesis

Biochemistry and genetics of inherited disorders of peroxisomal fatty acid metabolism

Genetic defects in dolichol metabolism

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