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MetaCyc Compound Class: a dolichyl phosphate

Synonyms: a a dolichol-phosphate, a dolychol phosphate, a dolichyl phosphate, a dolichol phosphate, a dolichyl monophosphate, a dolichol monophosphate

Summary:
Dolichol is the name given to a family of long-chain polyprenols that contain a varying number of cis-linked isoprene units, terminating with three trans-linked isoprene units. The first (alpha) unit in dolichols is always saturated [Sato01]. Additional modifications are found. For example, dolichols from certain halobacteria contain an additional saturation in the terminal (omega) isoprene unit.

The length of dolichol molecules varies within a range in a species, and the range varies among species (reviewed in [Burda99]). In mammals dolichols are usually within the range of 80 to 105 carbons. Archaebacteria prefer dolichols of 55-60 carbons.

Dolichyl phosphate acts as a membrane-bound carrier in the assembly of pyrophosphate-linked oligosaccharides. It can accept the respective sugar residues from the donors UDP-N-acetyl-α-D-glucosamine, UDP-α-D-glucose and GDP-α-D-mannose.

The structure shown here is of a C80 dolichol phosphate, containing 16 isoprene units.

a dolichyl phosphate compound structure

Chemical Formula: C80H131O4P

Instances:
ω-saturated C55 dolichol phosphate ,
ω-saturated C60 dolichol phosphate ,
C55 dolichol phosphate ,
C60 dolichol phosphate ,
C65 dolichol phosphate ,
C70 dolichol phosphate ,
C75 dolichol phosphate ,
C80 dolichol phosphate ,
C85 dolichol phosphate ,
C90 dolichol phosphate ,
C95 dolichol phosphate ,
C100 dolichol phosphate ,
C105 dolichol phosphate

Molecular Weight: 1187.9 Daltons

Monoisotopic Molecular Weight: 1188.9941492677 Daltons

SMILES: CC(=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(CCOP([O-])([O-])=O)C)C

InChI: InChI=1S/C80H133O4P/c1-65(2)33-18-34-66(3)35-19-36-67(4)37-20-38-68(5)39-21-40-69(6)41-22-42-70(7)43-23-44-71(8)45-24-46-72(9)47-25-48-73(10)49-26-50-74(11)51-27-52-75(12)53-28-54-76(13)55-29-56-77(14)57-30-58-78(15)59-31-60-79(16)61-32-62-80(17)63-64-84-85(81,82)83/h33,35,37,39,41,43,45,47,49,51,53,55,57,59,61,80H,18-32,34,36,38,40,42,44,46,48,50,52,54,56,58,60,62-64H2,1-17H3,(H2,81,82,83)/p-2/b66-35+,67-37+,68-39-,69-41-,70-43-,71-45-,72-47-,73-49-,74-51-,75-53-,76-55-,77-57-,78-59-,79-61-

InChIKey: InChIKey=BWKNNYLEGLXMHQ-AMBVJARFSA-L

Unification Links: ChEBI:16214 , KEGG:C00110 , PubChem:25244948

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 1512.6384 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

protein N-glycosylation (eukaryotic, high mannose) :
a dolichyl phosphate + UDP-α-D-glucose → a dolichyl β-D-glucosyl phosphate + UDP
a dolichyl phosphate + UDP-N-acetyl-α-D-glucosamine → an N-acetyl-α-D-glucosaminyl-diphosphodolichol + UMP
a dolichyl phosphate + GDP-α-D-mannose → a dolichyl β-D-mannosyl phosphate + GDP

Not in pathways:
a dolichyl phosphate + H2O → a dolichol + phosphate

Reactions known to produce the compound:

dolichol and dolichyl phosphate biosynthesis :
a dolichol + CTP → a dolichyl phosphate + CDP + H+

protein N-glycosylation (eukaryotic, high mannose) :
a (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-mannosyl phosphate[rough endoplasmic reticulum lumen] → a (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-glucosyl phosphate[rough endoplasmic reticulum lumen] → a glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-glucosyl phosphate[rough endoplasmic reticulum lumen] → a (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]
a (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl β-D-glucosyl phosphate[rough endoplasmic reticulum lumen] → a (glucosyl)3(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol[rough endoplasmic reticulum lumen] + a dolichyl phosphate[rough endoplasmic reticulum lumen] + H+[rough endoplasmic reticulum lumen]

Not in pathways:
a dolichyl β-D-mannosyl phosphate + H2O → a dolichyl phosphate + D-mannose + H+
a dolichyl β-D-glucosyl phosphate + H2O → a dolichyl phosphate + β-D-glucopyranose + H+

In Reactions of unknown directionality:

Not in pathways:
a dolichyl diphosphate + H2O = a dolichyl phosphate + phosphate + H+
a dolichyl diphosphate + (polyphosphate)(n) = a dolichyl phosphate + (polyphosphate)(n+1)
a dolichyl β-D-mannosyl phosphate + a [protein]-(L-serine/L-threonine) = a dolichyl phosphate + a [protein]-O-D-mannosyl-(L-serine/L-threonine) + H+
dolichyl D-xylosyl phosphate + a core protein L-serine = a dolichyl phosphate + O-β-D-xylosyl-[core protein] + H+
a (glucosyl)3(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + H2O = a dolichyl phosphate + (glucosyl)3-(mannosyl)9-(N-acetylglucosaminyl)2-phosphate + 2 H+
a dolichyl phosphate + UDP-N-acetyl-α-D-glucosamine = a dolichyl N-acetyl-α-D-glucosaminyl phosphate + UDP
a dolichyl phosphate + UDP-α-D-xylose = dolichyl D-xylosyl phosphate + UDP

Credits:
Revised 24-Aug-2010 by Caspi R , SRI International


References

Burda99: Burda P, Aebi M (1999). "The dolichol pathway of N-linked glycosylation." Biochim Biophys Acta 1426(2);239-57. PMID: 9878760

Fedorow05: Fedorow H, Pickford R, Hook JM, Double KL, Halliday GM, Gerlach M, Riederer P, Garner B (2005). "Dolichol is the major lipid component of human substantia nigra neuromelanin." J Neurochem 92(4);990-5. PMID: 15686500

Guan10: Guan Z, Naparstek S, Kaminski L, Konrad Z, Eichler J (2010). "Distinct glycan-charged phosphodolichol carriers are required for the assembly of the pentasaccharide N-linked to the Haloferax volcanii S-layer glycoprotein." Mol Microbiol 78(5);1294-303. PMID: 21091511

Kuntz97: Kuntz C, Sonnenbichler J, Sonnenbichler I, Sumper M, Zeitler R (1997). "Isolation and characterization of dolichol-linked oligosaccharides from Haloferax volcanii." Glycobiology 7(7);897-904. PMID: 9363431

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Sato01: Sato M, Fujisaki S, Sato K, Nishimura Y, Nakano A (2001). "Yeast Saccharomyces cerevisiae has two cis-prenyltransferases with different properties and localizations. Implication for their distinct physiological roles in dolichol synthesis." Genes Cells 6(6);495-506. PMID: 11442630


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Sat Aug 1, 2015, biocyc13.