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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 with a saturated α-isoprenoid unit [Sato01]. The length of dolichol molecules varies within a range in a species, and the range varies among species (reviewed in [Burda99]). A C80 dolichol with 16 isoprenoid units is shown is this structure.

Dolichyl phosphate acts as the carrier in the assembly of pyrophosphate-linked oligosaccharides, and is also the acceptor in the synthesis of the sugar donors a dolichyl β-D-mannosyl phosphate and a dolichyl β-D-glucosyl phosphate from GDP-Man and UDP-Glc, respectively.

Click on the "dolichol" group in the structure to see the full structure.

Chemical Formula: C80H131O4P

Instances:
dolichol14-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-/t80-/m0/s1

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:

dolichyl-diphosphooligosaccharide biosynthesis :
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-acetylglucosaminyl-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+

dolichyl-diphosphooligosaccharide biosynthesis :
a (mannosyl)5-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-mannosyl phosphate → a (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl phosphate + H+
a (mannosyl)6-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-mannosyl phosphate → a (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl phosphate + H+
a (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-mannosyl phosphate → a (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl phosphate + H+
a (mannosyl)7-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-mannosyl phosphate → a (mannosyl)8-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl phosphate + H+
a (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-glucosyl phosphate → dolichyl diphosphooligosaccharide + a dolichyl phosphate + H+
a (mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-glucosyl phosphate → a glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl phosphate + H+
a glucosyl-(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl β-D-glucosyl phosphate → a (glucosyl)2(mannosyl)9-(N-acetylglucosaminyl)2-diphosphodolichol + a dolichyl phosphate + H+

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-glucose + H+

In Reactions of unknown directionality:

Not in pathways:
dolichyl diphosphate + H2O = a dolichyl phosphate + phosphate + H+
a dolichyl β-D-mannosyl phosphate + a protein = a dolichyl phosphate + an O-D-mannosyl-protein
dolichyl diphosphooligosaccharide + H2O = a dolichyl phosphate + oligosaccharide phosphate + 2 H+
dolichyl D-xylosyl phosphate + a protein = a dolichyl phosphate + D-xylosylprotein
dolichyl diphosphate + (polyphosphate)(n) = a dolichyl phosphate + (polyphosphate)(n+1)
a dolichyl phosphate + UDP-α-D-xylose = dolichyl D-xylosyl phosphate + UDP
a dolichyl phosphate + UDP-N-acetyl-α-D-glucosamine = dolichyl N-acetyl-α-D-glucosaminyl 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

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


Report Errors or Provide Feedback
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 18.5 on Mon Nov 24, 2014, BIOCYC13B.