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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:03 UTC
HMDB IDHMDB0001265
Secondary Accession Numbers
  • HMDB0062489
  • HMDB01265
  • HMDB62489
Metabolite Identification
Common NameFucose 1-phosphate
DescriptionFucose 1-phosphate (CAS: 16562-58-6) belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphate group linked to the carbohydrate unit. Fucose 1-phosphate is an intermediate in the reversible synthesis of GDP-L-fucose catalyzed by the enzyme guanosine triphosphate fucose pyrophosphorylase (GFPP, EC 2.7.7.30). The reversible reaction is magnesium-dependent, although the enzyme is partially active when cobalt or manganese is substituted. The reaction is unusual in that, of the four canonical nucleoside triphosphates, only guanosine can be utilized efficiently to form a nucleotide-sugar. Free cytosolic fucose is phosphorylated by L-fucokinase (EC 2.7.1.52) to form fucose-1-phosphate in the salvage pathway of GDP-L-fucose (PMID: 16185085 , 14686921 ).
Structure
Thumb
Synonyms
Chemical FormulaC6H13O8P
Average Molecular Weight244.136
Monoisotopic Molecular Weight244.034804377
IUPAC Name{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphonic acid
Traditional Namefucose 1-phosphate
CAS Registry Number16562-59-7
SMILES
C[C@@H]1O[C@H](OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6+/m0/s1
InChI KeyPTVXQARCLQPGIR-SXUWKVJYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022520
KNApSAcK IDNot Available
Chemspider ID58841
KEGG Compound IDC02985
BioCyc IDCPD-488
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6120
PubChem Compound65369
PDB IDNot Available
ChEBI ID12387
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Quirk S, Seley KL: Identification of catalytic amino acids in the human GTP fucose pyrophosphorylase active site. Biochemistry. 2005 Oct 4;44(39):13172-8. [PubMed:16185085 ]
  2. Niittymaki J, Mattila P, Roos C, Huopaniemi L, Sjoblom S, Renkonen R: Cloning and expression of murine enzymes involved in the salvage pathway of GDP-L-fucose. Eur J Biochem. 2004 Jan;271(1):78-86. [PubMed:14686921 ]

Enzymes

General function:
Involved in fucose-1-phosphate guanylyltransferase acti
Specific function:
Catalyzes the formation of GDP-L-fucose from GTP and L-fucose-1-phosphate. Functions as a salvage pathway to reutilize L-fucose arising from the turnover of glycoproteins and glycolipids.
Gene Name:
FPGT
Uniprot ID:
O14772
Molecular weight:
37630.405
Reactions
Guanosine triphosphate + Fucose 1-phosphate → Pyrophosphate + GDP-L-fucosedetails
General function:
Involved in ATP binding
Specific function:
Takes part in the salvage pathway for reutilization of fucose from the degradation of oligosaccharides.
Gene Name:
FUK
Uniprot ID:
Q8N0W3
Molecular weight:
117621.795
Reactions
Adenosine triphosphate + L-Fucose → ADP + Fucose 1-phosphatedetails