Record Information
Version2.0
Creation Date2012-05-31 14:01:59 -0600
Update Date2015-06-03 15:54:36 -0600
Secondary Accession Numbers
  • ECMDB04010
Identification
Name:alpha,alpha-Trehalose 6-phosphate
DescriptionTrehalose 6-phosphate is synthesized by the E. coli gene product of otsA. It catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate.
Structure
Thumb
Synonyms:
  • α,α-trehalose 6-phosphate
  • α,α-trehalose 6-phosphoric acid
  • a,a-Trehalose 6-phosphate
  • a,a-Trehalose 6-phosphoric acid
  • a,Alpha'-trehalose 6-phosphate
  • a,Alpha'-trehalose 6-phosphoric acid
  • Alpha,alpha'-Trehalose 6-phosphate
  • alpha,Alpha'-trehalose 6-phosphoric acid
  • Alpha,alpha-Trehalose 6-phosphate
  • alpha,alpha-Trehalose 6-phosphoric acid
  • Tre6P
  • Trehalose 6-phosphate
  • Trehalose 6-phosphoric acid
  • Trehalose phosphate
  • Trehalose phosphoric acid
  • Trehalose-6-phosphate
  • Trehalose-6-phosphoric acid
  • α,Alpha'-trehalose 6-phosphate
  • α,Alpha'-trehalose 6-phosphoric acid
  • α,α-Trehalose 6-phosphate
  • α,α-Trehalose 6-phosphoric acid
Chemical Formula:C12H23O14P
Weight:Average: 422.2764
Monoisotopic: 422.082541956
InChI Key:LABSPYBHMPDTEL-UHFFFAOYSA-N
InChI:InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)
CAS number:4484-88-2
IUPAC Name:[(3,4,5-trihydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)methoxy]phosphonic acid
Traditional IUPAC Name:(3,4,5-trihydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)methoxyphosphonic acid
SMILES:OCC1OC(OC2OC(COP(O)(O)=O)C(O)C(O)C2O)C(O)C(O)C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentDisaccharide phosphates
Alternative Parents
Substituents
  • Disaccharide phosphate
  • Glycosyl compound
  • O-glycosyl compound
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Acetal
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility40.6 g/LALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area236.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.21 m³·mol⁻¹ChemAxon
Polarizability36.12 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
Trehalose Degradation I (low osmolarity)PW002097 ThumbThumb?image type=greyscaleThumb?image type=simple
trehalose biosynthesis IPW002088 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_19) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0950200000-892f27ada42528b88923View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-1940000000-562cf60e2df9ae537d3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-80b677accd914bdf5cdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05di-9540400000-a224ab96a48be27b9eb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9210000000-bc2b2577f83fa445d854View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0024eb099e0b2c51e332View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18283
HMDB IDHMDB01124
Pubchem Compound ID122336
Kegg IDC00689
ChemSpider ID1112
Wikipedia IDNot Available
BioCyc IDTREHALOSE-6P
EcoCyc IDTREHALOSE-6P

Enzymes

General function:
Involved in catalytic activity
Specific function:
Alpha,alpha-trehalose 6-phosphate + H(2)O = D- glucose + D-glucose 6-phosphate
Gene Name:
treC
Uniprot ID:
P28904
Molecular weight:
63837
Reactions
Alpha,alpha-trehalose 6-phosphate + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of glucose from UDP-glucose to glucose-6-phosphate to form alpha,alpha-1,1 trehalose-6-phosphate. Acts with retention of the anomeric configuration of the UDP-sugar donor. Essential for viability of the cells at low temperatures and at elevated osmotic strength
Gene Name:
otsA
Uniprot ID:
P31677
Molecular weight:
53611
Reactions
UDP-glucose + D-glucose 6-phosphate = UDP + alpha,alpha-trehalose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Removes the phosphate from trehalose 6-phosphate to produce free trehalose
Gene Name:
otsB
Uniprot ID:
P31678
Molecular weight:
29175
Reactions
Trehalose 6-phosphate + H(2)O = trehalose + phosphate.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in trehalose transport
Gene Name:
treB
Uniprot ID:
P36672
Molecular weight:
51080
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:
crr
Uniprot ID:
P69783
Molecular weight:
18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.

Transporters

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in trehalose transport
Gene Name:
treB
Uniprot ID:
P36672
Molecular weight:
51080
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.