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Trehalose (YMDB00008)

Identification
YMDB IDYMDB00008
NameTrehalose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTrehalose is a non-reducing disaccharide formed by a 1,1-glucoside bond between two alpha-glucose units. In nature, trehalose can be found in animals, plants, and microorganisms. It is implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (GLC)2
  • a-D-GLCP-(11)-a-D-GLCP
  • a-D-Glucopyranosyl-a-D-glucopyranoside
  • a-D-Trehalose
  • a-Trehalose
  • a,Alpha'-trehalose
  • alpha-D-GLCP-(11)-alpha-D-GLCP
  • alpha-D-Glucopyranosyl-alpha-D-glucopyranoside
  • alpha-D-Trehalose
  • alpha-Trehalose
  • alpha,alpha-trehalose
  • alpha,Alpha'-trehalose
  • D-(+)-Trehalose
  • D-trehalose-anhydrous
  • delta-trehalose-anhydrous
  • Ergot sugar
  • Mycose
  • α-D-GLCP-(11)-α-D-GLCP
  • α-D-glucopyranosyl-α-D-glucopyranoside
  • α-D-trehalose
  • α-trehalose
  • α,alpha'-trehalose
  • Α,alpha'-trehalose
  • Α-D-GLCP-(11)-α-D-GLCP
  • Α-D-glucopyranosyl-α-D-glucopyranoside
  • Α-D-trehalose
  • Α-trehalose
CAS number99-20-7
WeightAverage: 342.2965
Monoisotopic: 342.116211546
InChI KeyHDTRYLNUVZCQOY-LIZSDCNHSA-N
InChIInChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
Traditional IUPAC Nameα,α'-trehalose
Chemical FormulaC12H22O11
SMILES[H]OC([H])([H])[C@@]1([H])O[C@]([H])(O[C@@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point203 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility592 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.2 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • vacuole
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Trehalose 6-phosphate + water ↔ Trehalose + phosphate
Trehalose + water ↔ D-Glucose
KEGG Reactions
water + Trehalose → D-Glucose
water + Trehalose 6-phosphate → phosphate + Trehalose
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
24290 ± 9522 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kim, J., Alizadeh, P., Harding, T., Hefner-Gravink, A., Klionsky, D. J. (1996). "Disruption of the yeast ATH1 gene confers better survival after dehydration, freezing, and ethanol shock: potential commercial applications." Appl Environ Microbiol 62:1563-1569.8633854
  • Lewis, J. G., Learmonth, R. P., Watson, K. (1995). "Induction of heat, freezing and salt tolerance by heat and salt shock in Saccharomyces cerevisiae." Microbiology 141 ( Pt 3):687-694.7711907
  • van der Plaat, J. B. (1974). "Cyclic 3',5'-adenosine monophosphate stimulates trehalose degradation in baker's yeast." Biochem Biophys Res Commun 56:580-587.4363744
  • Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Hans, M. A., Heinzle, E., Wittmann, C. (2003). "Free intracellular amino acid pools during autonomous oscillations in Saccharomyces cerevisiae." Biotechnol Bioeng 82:143-151.12584756
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • De Virgilio, C., Burckert, N., Bell, W., Jeno, P., Boller, T., Wiemken, A. (1993). "Disruption of TPS2, the gene encoding the 100-kDa subunit of the trehalose-6-phosphate synthase/phosphatase complex in Saccharomyces cerevisiae, causes accumulation of trehalose-6-phosphate and loss of trehalose-6-phosphate phosphatase activity." Eur J Biochem 212:315-323.8444170
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Murao, Sawao; Nagano, Hiroto; Ogura, Sei; Nishino, Toyokazu. Enzymic synthesis of trehalose from maltose. Agricultural and Biological Chemistry (1985), 49(7), 2113-18.
External Links:
ResourceLink
CHEBI ID16551
HMDB IDHMDB00975
Pubchem Compound ID1143
Kegg IDC01083
ChemSpider ID24727757
FOODB IDFDB001114
WikipediaTrehalose
BioCyc IDTREHALOSE

Enzymes

Protein Details
1. Probable trehalase
General function:
Involved in catalytic activity
Specific function:
Alpha,alpha-trehalose + H(2)O = 2 D-glucose
Gene Name:
NTH2
Uniprot ID:
P35172
Molecular weight:
89678.60156
Reactions
Alpha,alpha-trehalose + H(2)O → 2 D-glucose.
Protein Details
2. Vacuolar acid trehalase
General function:
Involved in catalytic activity
Specific function:
Alpha,alpha-trehalose + H(2)O = 2 D-glucose
Gene Name:
ATH1
Uniprot ID:
P48016
Molecular weight:
136919.0
Reactions
Alpha,alpha-trehalose + H(2)O → 2 D-glucose.
Protein Details
3. Neutral trehalase
General function:
Involved in catalytic activity
Specific function:
Alpha,alpha-trehalose + H(2)O = 2 D-glucose
Gene Name:
NTH1
Uniprot ID:
P32356
Molecular weight:
85878.5
Reactions
Alpha,alpha-trehalose + H(2)O → 2 D-glucose.
Protein Details
4. Trehalose-phosphatase
General function:
Involved in catalytic activity
Specific function:
Phosphatase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process
Gene Name:
TPS2
Uniprot ID:
P31688
Molecular weight:
102976.0
Reactions
Trehalose 6-phosphate + H(2)O → trehalose + phosphate.
Protein Details
5. Alpha,alpha-trehalose-phosphate synthase [UDP-forming] 56 kDa subunit
General function:
Involved in catalytic activity
Specific function:
Synthase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. Can function independently of the complex
Gene Name:
TPS1
Uniprot ID:
Q00764
Molecular weight:
56147.5
Reactions
UDP-glucose + D-glucose 6-phosphate → UDP + alpha,alpha-trehalose 6-phosphate.
Protein Details
6. Trehalose synthase complex regulatory subunit TPS3
General function:
Involved in catalytic activity
Specific function:
Regulatory subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. May stabilize the trehalose synthase complex
Gene Name:
TPS3
Uniprot ID:
P38426
Molecular weight:
118834.0
Reactions