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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:30:01 UTC
HMDB IDHMDB00994
Secondary Accession NumbersNone
Metabolite Identification
Common NameDolichyl phosphate D-mannose
DescriptionDolichyl phosphate D-mannose (DPM) is an intermediate in the biosynthesis of N-glycans. It is a substrate for dolichol-phosphate mannosyltransferase (PMID: 10835346 ). Dolichol-phosphate mannosyltransferase is a heterotrimeric protein embedded in the endoplasmic reticulum membrane. The first subunit of the heterotrimer appears to be the actual catalyst, and the other two subunits appear to stabilize it. More specifically, dolichol-phosphate-mannose is the donor of mannose groups in the synthesis of the dolichol pyrophosphate-linked precursor oligosaccharide in asparagine-linked glycosylation, in the synthesis of glycosyl phosphatidylinositol (GPI) anchor precursors, in protein O-mannosylation and in protein C-mannosylation. Its synthesis proceeds in two steps. First, cytosolic GDP-mannose reacts with dolichol phosphate exposed on the cytosolic face of the endoplasmic reticulum membrane to form DPM with its mannose moiety oriented toward the cytosol. The DPM molecule then flips in the endoplasmic reticulum membrane, so that its mannose moiety is in the endoplasmic reticulum lumen, accessible to the enzymes that catalyze its transfer to growing glycolipids and glycoproteins. (PMID: 11102867 ). Dolichyl phosphate D-mannose is also a substrate for protein O-mannosyl-transferase 2 and protein O-mannosyl-transferase 1.
Structure
Thumb
Synonyms
  1. Dolichol phosphate mannose
  2. Dolichyl D-mannosyl phosphate
  3. Dolichyl phosphate D-mannose
  4. DPM
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional Name[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
CAS Registry Number908211-94-9
SMILES
OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1
InChI KeyHXXFSFRBOHSIMQ-PQMKYFCFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of N-Glycan biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility32.3ALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m3·mol-1ChemAxon
Polarizability20.33 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022356
KNApSAcK IDNot Available
Chemspider ID2496902
KEGG Compound IDC03862
BioCyc IDCPD-171
BiGG ID1809321
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00994
Metagene LinkHMDB00994
METLIN ID5925
PubChem Compound3246168
PDB IDNot Available
ChEBI ID1220424
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Maeda Y, Tanaka S, Hino J, Kangawa K, Kinoshita T: Human dolichol-phosphate-mannose synthase consists of three subunits, DPM1, DPM2 and DPM3. EMBO J. 2000 Jun 1;19(11):2475-82. Pubmed: 10835346
  2. Kinoshita T, Inoue N: Dissecting and manipulating the pathway for glycosylphos-phatidylinositol-anchor biosynthesis. Curr Opin Chem Biol. 2000 Dec;4(6):632-8. Pubmed: 11102867

Enzymes

General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Transfers mannose from GDP-mannose to dolichol monophosphate to form dolichol phosphate mannose (Dol-P-Man) which is the mannosyl donor in pathways leading to N-glycosylation, glycosyl phosphatidylinositol membrane anchoring, and O-mannosylation of proteins.
Gene Name:
DPM1
Uniprot ID:
O60762
Molecular weight:
29633.995
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannosyl residues to the hydroxyl group of serine or threonine residues. Coexpression of both POMT1 and POMT2 is necessary for enzyme activity, expression of either POMT1 or POMT2 alone is insufficient.
Gene Name:
POMT1
Uniprot ID:
Q9Y6A1
Molecular weight:
82566.18
Reactions
Dolichyl phosphate D-mannose + protein → Dolichol-20 + O-D-mannosylproteindetails
General function:
Involved in mannosyltransferase activity
Specific function:
Transfers mannosyl residues to the hydroxyl group of serine or threonine residues. Coexpression of both POMT1 and POMT2 is necessary for enzyme activity, expression of either POMT1 or POMT2 alone is insufficient.
Gene Name:
POMT2
Uniprot ID:
Q9UKY4
Molecular weight:
84213.155
Reactions
Dolichyl phosphate D-mannose + protein → Dolichol-20 + O-D-mannosylproteindetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Adds the first Dol-P-Man derived mannose in an alpha-1,3 linkage to Man5GlcNAc2-PP-Dol.
Gene Name:
ALG3
Uniprot ID:
Q92685
Molecular weight:
44369.995
Reactions
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Not Available
Specific function:
Adds the eighth mannose residue in an alpha-1,6 linkage onto the dolichol-PP-oligosaccharide precursor (dolichol-PP-Man(7)GlcNAc(2)) required for protein glycosylation.
Gene Name:
ALG12
Uniprot ID:
Q9BV10
Molecular weight:
54654.195
Reactions
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Not Available
Specific function:
Catalyzes the transfer of mannose from Dol-P-Man to lipid-linked oligosaccharides.
Gene Name:
ALG9
Uniprot ID:
Q9H6U8
Molecular weight:
69862.66
Reactions
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
Dolichyl phosphate D-mannose + D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol → D-Man-alpha-(1->2)-D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-[D-Man-alpha-(1->2)-D-Man-alpha-(1->3)-(D-Man-alpha-(1->2)-D-Man-alpha-(1->6))-D-Man-alpha-(1->6)]-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol + Dolichol-20details
General function:
Not Available
Specific function:
Regulates the biosynthesis of dolichol phosphate-mannose. Essential for the ER localization and stable expression of DPM1.
Gene Name:
DPM2
Uniprot ID:
O94777
Molecular weight:
Not Available
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
General function:
Not Available
Specific function:
Stabilizer subunit of the dolichol-phosphate-mannose synthase complex.
Gene Name:
DPM3
Uniprot ID:
Q9P2X0
Molecular weight:
Not Available
Reactions
Guanosine diphosphate mannose + Dolichol-20 → Guanosine diphosphate + Dolichyl phosphate D-mannosedetails