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Trehalose (YMDB00008)

Identification
YMDB IDYMDB00008
NameTrehalose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTrehalose, also known as alpha-D-trehalose or (GLC)2, 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. Trehalose is an extremely weak basic (essentially neutral) compound (based on its pKa). Trehalose exists in all living species, ranging from bacteria to humans. Within yeast, trehalose participates in a number of enzymatic reactions. In particular, trehalose can be biosynthesized from trehalose 6-phosphate through the action of the enzyme trehalose 6-phosphate synthase. In addition, trehalose can be converted into D-glucose through the action of the enzyme alpha,alpha-trehalase. In yeast, trehalose is involved in the metabolic pathway called the starch and sucrose metabolism pathway.
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