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L-Sorbose (YMDB00204)

Identification
YMDB IDYMDB00204
NameL-Sorbose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionL-Sorbose, also known as L-sorbinose or L-xylo-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. L-Sorbose is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Sorbose exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • alpha-L-Sorbopyranose
  • hex-2-ulose
  • L-(-)-Sorbose
  • L-1,3,4,5,6-Pentahydroxyhexan-2-one
  • L-Sorbinose
  • L-Sorbose
  • L-xylo-2-Hexulose
  • l-xylo-hexulose
  • L(-)-Sorbose
  • Sorbin
  • Sorbinose
  • Sorbose
  • xylo-Hexulose
  • L(-) Sorbose for biochemistry
  • L-(-)-Sorbose 99%
  • alpha-L-Xylo-hexopyranos-2-ulose
  • Α-L-xylo-hexopyranos-2-ulose
  • Α-L-sorbopyranose
  • a-L-Sorbopyranose
CAS number87-79-6
WeightAverage: 180.1559
Monoisotopic: 180.063388116
InChI KeyLKDRXBCSQODPBY-BGPJRJDNSA-N
InChIInChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1
IUPAC Name(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Nameα-L-sorbopyranose
Chemical FormulaC6H12O6
SMILES[H]OC([H])([H])[C@@]1(O[H])OC([H])([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 monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point165 °C
Experimental Properties
PropertyValueReference
Water Solubility360 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1190 g/LALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
BitterFDB001126
SMPDB PathwaysNot Available
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
SMPDB ReactionsNot Available
KEGG Reactions
NAD + L-glucitol → NADH + hydron + L-Sorbose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-9700000000-3e5e0a3aa6c676c97701JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-8422790000-fda815da7846441c6ea7JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-ad56c2283c4948268668JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ri-9600000000-f53f9ae5db12b8c07611JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0079-9200000000-c3dabd4edd0fd062cfd4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-014681a0ceccca243630JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-2900000000-fdd4f1c2b01b7cd4a621JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c30-9200000000-a3afc1e71049f23145b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fu-9700000000-86b1b9f75df959e2158fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-024i-9800000000-1acd95dd1e6f8744308fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-545f59c3707e4298b57cJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
Synthesis Reference:Banjopnoppakun, Tanaphat; Moonmangmee, Somporn; Moonmangmee, Duangtip. Production of L-sorbose by thermotolerant acetic acid bacteria. Proceeding of the Kasetsart University Annual Conference, 44th, Bangkok, Thailand, Jan. 30-Feb. 2, 2006 (2006),
External Links:
ResourceLink
CHEBI ID17266
HMDB IDHMDB01266
Pubchem Compound ID439192
Kegg IDC00247
ChemSpider ID23936183
FOODB IDFDB001126
WikipediaSorbose
BioCyc IDSORBOSE

Enzymes

Protein Details
1. Sorbitol dehydrogenase 1
General function:
Involved in zinc ion binding
Specific function:
L-iditol + NAD(+) = L-sorbose + NADH
Gene Name:
SOR1
Uniprot ID:
P35497
Molecular weight:
38165.39844
Reactions
L-iditol + NAD(+) → L-sorbose + NADH.
Protein Details
2. Sorbitol dehydrogenase 2
General function:
Involved in zinc ion binding
Specific function:
L-iditol + NAD(+) = L-sorbose + NADH
Gene Name:
SOR2
Uniprot ID:
Q07786
Molecular weight:
38096.30078
Reactions
L-iditol + NAD(+) → L-sorbose + NADH.