Record Information
Version2.0
Creation Date2012-05-31 14:02:34 -0600
Update Date2015-09-13 12:56:13 -0600
Secondary Accession Numbers
  • ECMDB04025
Identification
Name:beta-D-Galactose
DescriptionGalactose is an optical isomer of glucose. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Galactose is less sweet than glucose and not very water-soluble. Galactose is a monosaccharide constituent, together with glucose, of the disaccharide lactose. Galactose is produced by hydrolysis of lactose by galactosidase. This enzyme is produced by the lac operon in Escherichia coli (E. coli). Galactan is a polymer of the sugar galactose. It is found in hemicellulose and can be converted to galactose by hydrolysis.
Structure
Thumb
Synonyms:
  • 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
  • b D-Galactose
  • b-D-Galactopyranose
  • B-D-Galactose
  • B-D-Galactoside
  • b-D-Galactosides
  • b-delta-Galactoside
  • b-delta-Galactosides
  • B-Galactose
  • b-δ-Galactoside
  • b-δ-Galactosides
  • Beta D-Galactose
  • Beta-D-Galactopyranose
  • Beta-D-Galactose
  • Beta-D-Galactoside
  • Beta-D-Galactosides
  • Beta-delta-Galactoside
  • Beta-delta-galactosides
  • Beta-Galactose
  • Cerebrose
  • D-galactose
  • Delta-Galactose
  • Galactopyranose
  • Galactopyranoside
  • Galactose
  • β D-Galactose
  • β-D-Galactopyranose
  • β-D-Galactose
  • β-D-Galactoside
  • β-D-Galactosides
  • β-Galactose
  • β-δ-Galactoside
  • β-δ-Galactosides
  • δ-Galactose
Chemical Formula:C6H12O6
Weight:Average: 180.1559
Monoisotopic: 180.063388116
InChI Key:WQZGKKKJIJFFOK-FPRJBGLDSA-N
InChI:InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6-/m1/s1
CAS number:7296-64-2
IUPAC Name:(2R,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name:β D-galactose
SMILES:OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
galactose degradation/Leloir PathwayPW000884 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-3900000000-3b00dcca100b6e3bb228View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-9000000000-867bfd833e01f3033747View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-066r-9000000000-65a7d765a9429db38b1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398View in MoNA
References
References:
  • Bhavanandan VP, Puch S, Guo X, Jiang W: Galectins and other endogenous carbohydrate-binding proteins of animal bladder. Adv Exp Med Biol. 2001;491:95-108. Pubmed: 14533792
  • Chen YT, Mattison DR, Bercu BB, Schulman JD: Resistance of the male gonad to a high galactose diet. Pediatr Res. 1984 Apr;18(4):345-8. Pubmed: 6718090
  • Furuhashi M, Suzuki S, Tomoda Y, Suganuma N: Role of the Pro-Leu-Arg motif in glycosylation of human gonadotropin alpha-subunit. Endocrinology. 1995 May;136(5):2270-5. Pubmed: 7536667
  • Goluboff ET, Mertz JR, Tres LL, Kierszenbaum AL: Galactosyl receptor in human testis and sperm is antigenically related to the minor C-type (Ca(2+)-dependent) lectin variant of human and rat liver. Mol Reprod Dev. 1995 Apr;40(4):460-6. Pubmed: 7598912
  • Hanisch FG, Heimbuchel G, Baldus SE, Uhlenbruck G, Schmits R, Pfreundschuh M, Schwonzen M, Vierbuchen M, Bara J, Peter-Katalinic J: Monoclonal antibody FW6 defines an epitope on alpha 3/4-monofucosylated polylactosaminoglycans expressed by fetal and colon carcinoma-associated mucins. Cancer Res. 1993 Sep 15;53(18):4367-75. Pubmed: 8364932
  • Kalichman MW, Powell HC, Mizisin AP: Reactive, degenerative, and proliferative Schwann cell responses in experimental galactose and human diabetic neuropathy. Acta Neuropathol (Berl). 1998 Jan;95(1):47-56. Pubmed: 9452821
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Mizoguchi N, Ono H, Eguchi T, Sakura N: Galactose metabolites in blood from neonates with and without hypergalactosaemia detected by mass screening. Eur J Pediatr. 2000 Nov;159(11):851-3. Pubmed: 11079200
  • Muthusamy A, Erickson DR, Sheykhnazari M, Bhavanandan VP: Enhanced binding of modified pentosan polysulfate and heparin to bladder--a strategy for improved treatment of interstitial cystitis. Urology. 2006 Jan;67(1):209-13. Pubmed: 16413377
  • Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. Pubmed: 3757018
  • Niebroj-Dobosz I, Janik P, Jamrozik Z, Kwiecinski H: Immunochemical quantification of glycoconjugates in serum and cerebrospinal fluid of amyotrophic lateral sclerosis patients. Eur J Neurol. 1999 May;6(3):335-40. Pubmed: 10210915
  • Ning C, Reynolds R, Chen J, Yager C, Berry GT, McNamara PD, Leslie N, Segal S: Galactose metabolism by the mouse with galactose-1-phosphate uridyltransferase deficiency. Pediatr Res. 2000 Aug;48(2):211-7. Pubmed: 10926297
  • Ono H, Mawatari H, Mizoguchi N, Eguchi T, Sakura N, Hamakawa M: Transient galactosemia detected by neonatal mass screening. Pediatr Int. 1999 Jun;41(3):281-4. Pubmed: 10365579
  • Puch S, Bhavanandan VP: Endogenous carbohydrate-binding proteins of rabbit and human bladder. Urology. 1999 Apr;53(4):848-52. Pubmed: 10197873
  • Rapoport EM, Nekrasov MV, Khaidukov SV, Svirshchevskaya EV, Zhigis LS, Kozlov LV, Batalova TN, Zubov VP, Bovin NV: Cellular localization of the galactose-binding lectin from human serum. Biochemistry (Mosc). 2000 Nov;65(11):1316-20. Pubmed: 11112850
  • Schmidt LE, Ott P, Tygstrup N: Galactose elimination capacity as a prognostic marker in patients with severe acetaminophen-induced hepatotoxicity: 10 years' experience. Clin Gastroenterol Hepatol. 2004 May;2(5):418-24. Pubmed: 15118981
  • Seiler CA, Renner EL, Czerniak A, Didonna D, Buchler MW, Reichen J: Early acute cellular rejection: no effect on late hepatic allograft function in man. Transpl Int. 1999;12(3):195-201. Pubmed: 10429957
  • Stanley A, Osler T: Senescence and the healing rates of venous ulcers. J Vasc Surg. 2001 Jun;33(6):1206-11. Pubmed: 11389419
  • Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
  • van den Nieuwenhof IM, Renardel de Lavalette C, Diaz N, van Die I, van den Berg TK: Differential galactosylation of neuronal and haematopoietic signal regulatory protein-alpha determines its cellular binding-specificity. J Cell Sci. 2001 Apr;114(Pt 7):1321-9. Pubmed: 11256998
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Wan H, Perez DR: Quail carry sialic acid receptors compatible with binding of avian and human influenza viruses. Virology. 2006 Mar 15;346(2):278-86. Epub 2005 Dec 2. Pubmed: 16325879
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Wolfrom, M. L.; Thompson, A.; Inatome, M. Acyl migration in the D-galactose structure. Journal of the American Chemical Society (1957), 79 3868-71.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID27667
HMDB IDHMDB03449
Pubchem Compound ID439353
Kegg IDC00962
ChemSpider ID388476
WikipediaGAL
BioCyc IDGALACTOSE
EcoCyc IDGALACTOSE
Ligand ExpoGLB

Enzymes

General function:
Involved in beta-galactosidase activity
Specific function:
Hydrolysis of terminal non-reducing beta-D- galactose residues in beta-D-galactosides
Gene Name:
lacZ
Uniprot ID:
P00722
Molecular weight:
116482
Reactions
Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides.
General function:
Involved in aldose 1-epimerase activity
Specific function:
Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose
Gene Name:
galM
Uniprot ID:
P0A9C3
Molecular weight:
38190
Reactions
Alpha-D-glucose = beta-D-glucose.
General function:
Carbohydrate transport and metabolism
Specific function:
Specific function unknown
Gene Name:
ytfQ
Uniprot ID:
P39325
Molecular weight:
34344
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for galactoside. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
mglC
Uniprot ID:
P23200
Molecular weight:
35550

Transporters

General function:
Involved in transporter activity
Specific function:
Responsible for melibiose transport. It is capable of using hydrogen, sodium, and lithium cations as coupling cations for cotransport, depending on the particular sugar transported (symport system)
Gene Name:
melB
Uniprot ID:
P02921
Molecular weight:
52217
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs. Can transport IPTG, lactose and glucose. Has broad substrate specificity, with preferences for glucosides or galactosides with alkyl or aryl substituents
Gene Name:
setA
Uniprot ID:
P31675
Molecular weight:
42713
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
General function:
Carbohydrate transport and metabolism
Specific function:
Specific function unknown
Gene Name:
ytfQ
Uniprot ID:
P39325
Molecular weight:
34344
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for galactoside. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
mglC
Uniprot ID:
P23200
Molecular weight:
35550
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368