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Xylitol (YMDB00778)

Identification
YMDB IDYMDB00778
NameXylitol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Xylitol, also known as meso-xylitol or xylisorb, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. D-Xylitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Within yeast, D-xylitol participates in a number of enzymatic reactions. In particular, D-xylitol can be converted into D-xylulose; which is catalyzed by the enzyme D-xylulose reductase. In addition, D-xylitol can be biosynthesized from D-xylose through the action of the enzyme trifunctional aldehyde reductase/xylose reductase/glucose 1-dehydrogenase (nadp(+)). In yeast, D-xylitol is involved in the metabolic pathway called the xylitol degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2R,3R,4S)-Pentane-1,2,3,4,5-pentaol
  • D-Xylitol
  • Eutrit
  • Fluorette
  • Klinit
  • Kylit
  • L-xylitol
  • meso-xylitol
  • Pentitol
  • Wood sugar alcohol
  • XLS
  • Xylit
  • Xylite
  • Xylitol
  • Xylitol C
  • Xyliton
  • xylo-Pentitol
  • Xylisorb
  • Xylisorb 300
  • Xylisorb 700
  • Xylitab 100
  • Xylitab 300
  • Xylitab DC
  • Xylite (sugar)
CAS number87-99-0
WeightAverage: 152.1458
Monoisotopic: 152.068473494
InChI KeyHEBKCHPVOIAQTA-SCDXWVJYSA-N
InChIInChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
IUPAC Name(2R,4S)-pentane-1,2,3,4,5-pentol
Traditional IUPAC Name(2R,4S)-pentane-1,2,3,4,5-pentol
Chemical FormulaC5H12O5
SMILESOC[C@H](O)[C@@H](O)[C@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point93.5 °C
Experimental Properties
PropertyValueReference
Water Solubility642 mg/mL [MERCK INDEX (1996)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
logP-3.1ChemAxon
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability14.48 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Extracellular
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB001134
SMPDB Pathways
xylitol degradationPW002433 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pentose and glucuronate interconversionsec00040 Map00040
SMPDB ReactionsNot Available
KEGG Reactions
NAD + Xylitol → NADH + D-Xylulose + hydron
aldehydo-D-Xylose + NADPH + hydron → NADP + Xylitol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0gb9-0962000000-d64d55ac02d5d037d679JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-0962000000-d64d55ac02d5d037d679JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0941000000-0d418fcb2879fa30315eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0941000000-1842afabd092c907a920JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-738016d8bd07caed9cccJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-9600000000-42440e0b7d380a297360JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-02t9-9000000000-d41bf19405e393c2be01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-9000000000-3d14b034f5655c90b890JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-4f856d537cc8252ecc47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-403bacad5117a30582dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-eb879b27e7b182cfe7c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9400000000-3db6454ab3e2315aa744JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9200000000-b84c400427c7e44eb4ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c37624fb31a8cb33b163JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
  • Richard, P., Toivari, M. H., Penttila, M. (1999). "Evidence that the gene YLR070c of Saccharomyces cerevisiae encodes a xylitol dehydrogenase." FEBS Lett 457:135-138.10486580
  • Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Hasumi, Fumihiko; Teshima, Chitoku; Okura, Ichiro. Synthesis of xylitol by reduction of xylulose with the combination of hydrogenase and xylulose reductase. Chemistry Letters (1996), (8), 597-598.
External Links:
ResourceLink
CHEBI ID17151
HMDB IDHMDB02917
Pubchem Compound ID6912
Kegg IDC00379
ChemSpider ID21391692
FOODB IDFDB001134
WikipediaXylitol
BioCyc IDCPD-496

Enzymes

Protein Details
1. D-xylulose reductase
General function:
Involved in zinc ion binding
Specific function:
Xylitol + NAD(+) = D-xylulose + NADH
Gene Name:
XYL2
Uniprot ID:
Q07993
Molecular weight:
38600.10156
Reactions
Xylitol + NAD(+) → D-xylulose + NADH.
Protein Details
2. NADPH-dependent aldose reductase GRE3
General function:
Involved in oxidoreductase activity
Specific function:
Reduces the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde similar to GRE2. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation. In pentose-fermenting yeasts, aldose reductase catalyzes the reduction of xylose into xylitol. The purified enzyme catalyzes this reaction, but the inability of S.cerevisiae to grow on xylose as sole carbon source indicates that the physiological function is more likely methylglyoxal reduction
Gene Name:
GRE3
Uniprot ID:
P38715
Molecular weight:
37118.5
Reactions
Alditol + NAD(P)(+) → aldose + NAD(P)H.
(R)-lactaldehyde + NADP(+) → methylglyoxal + NADPH.