Trehalose (YMDB00008)

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Identification

YMDB ID

YMDB00008

Name

Trehalose

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Trehalose, 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; which is mediated by the enzyme trehalose 6-phosphate synthase. In addition, trehalose can be converted into D-glucose; which is catalyzed by the enzyme alpha,alpha-trehalase. In yeast, trehalose is involved in the metabolic pathway called the starch and sucrose metabolism pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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
D-Trehalose
Natural trehalose
O-D-Glucopyranosyl-(1→1)-D-glucopyranoside
alpha,Alpha'-D-trehalose
alpha-D-Glucopyranosyl alpha-D-glucopyranoside
Α,α'-D-trehalose
Α,α-trehalose
Α,α’-D-trehalose
Α-D-glucopyranosyl α-D-glucopyranoside
Trehalose

CAS number

99-20-7

Weight

Average: 342.2965
Monoisotopic: 342.116211546

InChI Key

HDTRYLNUVZCQOY-LIZSDCNHSA-N

InChI

InChI=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 Name

α,α'-trehalose

Chemical Formula

C₁₂H₂₂O₁₁

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

trehalose (CHEBI:16551 )
Disaccharides (C01083 )

Physical Properties

State

Solid

Charge

Melting point

203 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	592 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.24	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	31.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
vacuole
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Starch and sucrose metabolism

PW002481

KEGG Pathways

Starch and sucrose metabolism

ec00500

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 Concentration	Substrate	Growth Conditions	Strain	Citation
24290 ± 9522 µM	Synthetic medium with 20 g/L glucose	aerobic	Baker's yeast	PMID: 12584756
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-0j4m-0932000000-8d7c80edd7f55e92ea29	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-00di-9511000000-b710c7c4bd86fd5f1af0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-00di-9511000000-2e5f22e6ba282283a569	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-00di-9832000000-b3259de2e25ea7293565	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-0wos-0921000000-68fb82f427417ec703a0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-0j4m-0943000000-07c11d483e4278dc639a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-0wmm-0953000000-b74403fa3ce6ce0339eb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0i04-0932000000-8de0421184ae3291ea53	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-00di-8932000000-c327fe31b8d3e86dd97d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (8 TMS)	splash10-0j4l-0954000000-33e230d28780be607983	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0j4m-0932000000-8d7c80edd7f55e92ea29	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9511000000-b710c7c4bd86fd5f1af0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9511000000-2e5f22e6ba282283a569	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9832000000-b3259de2e25ea7293565	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0wos-0921000000-68fb82f427417ec703a0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0j4m-0943000000-07c11d483e4278dc639a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0wmm-0953000000-b74403fa3ce6ce0339eb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0i04-0932000000-8de0421184ae3291ea53	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-8932000000-c327fe31b8d3e86dd97d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0j4l-0954000000-33e230d28780be607983	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0i2d-0921000000-9e633378baf1645df2a1	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08ni-9554000000-e418bec346785e269084	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-014i-2553419000-dd0bea0ade3ee46308dc	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-1901000000-865e9e390fac7d13c2f8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9500000000-7d4c9de285c2872d2320	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-c71f25d08b875caff6b6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0006-0019000000-3b4e276ff5686c841bdd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0fdx-8905000000-fafde7828ce0d63fe618	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fdx-8905000000-f4b4b3ad528ea3bf43c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-d382926500274fb84a46	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-10524d7a715f8a0ed265	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0019000000-3b4e276ff5686c841bdd	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03ec-0903000000-8981579ae1dd58ba65c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1901000000-4c8ec381daa00b88a539	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-5900000000-89485b49a32afa256bdc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-4918000000-df3152da1740bcb45d3d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03mi-3901000000-c9e67703b1ef9ca4f8cc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9600000000-b9d2971c377f79dd6238	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-022c-9100000000-33d1067ccb0cb2dda51d	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	16551
HMDB ID	HMDB00975
Pubchem Compound ID	1143
Kegg ID	C01083
ChemSpider ID	24727757
FOODB ID	FDB001114
Wikipedia	Trehalose
BioCyc ID	TREHALOSE

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

Structure for #<Compound:0xacdab89c>

Enzymes

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