D-Galactose (ECMDB00143) (M2MDB000054)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:21:49 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-06-03 15:53:14 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | D-Galactose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | D-Galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules. Metabolic pathways for D-Galactose are important not only for the provision of these pathways but also for the prevention of D-Galactose and D-Galactose metabolite accumulation. The main source of D-Galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-Galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-Galactose-1-phosphate. In the presence of D-Galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-Galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. (PMID: 15256214, 11020650, 10408771) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C6H12O6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 180.1559 Monoisotopic: 180.063388116 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | WQZGKKKJIJFFOK-SVZMEOIVSA-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: | 59-23-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | galactose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC[C@H]1OC(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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Hexoses | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 170 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + D-Galactose > ADP + D-Galactose + Hydrogen ion + Phosphate Adenosine triphosphate + Water + D-Galactose > ADP + D-Galactose + Hydrogen ion + Phosphate Adenosine triphosphate + D-Galactose + Alpha-D-Galactose <> ADP + Galactose 1-phosphate + Hydrogen ion Water + alpha-Lactose > D-Galactose + D-Glucose beta-D-Galactose > D-Galactose Galactose 1-phosphate + Water > D-Galactose + Phosphate Water + Melibiose > D-Galactose + D-Glucose Adenosine triphosphate + D-Galactose <> ADP + Galactose 1-phosphate Melibiose + Water <> D-Galactose + D-Glucose Raffinose + Water <> D-Galactose + Sucrose Galactosylglycerol + Water <> D-Galactose + Glycerol Galactan + Water <> D-Galactose + Galactan Galactinol + Water <> Inositol + D-Galactose Epimelibiose + Water <> D-Mannose + D-Galactose alpha-Lactose + Water <> alpha-D-Glucose + D-Galactose Melibiitol + Water <> Sorbitol + D-Galactose beta-D-Galactosyl-1,4-beta-D-glucosylceramide + Water <> Glucosylceramide + D-Galactose Stachyose + Water <> Raffinose + D-Galactose Digalactosylceramide + Water <> Galactosylceramide + D-Galactose Digalactosyl-diacylglycerol + Water <> 1,2-Diacyl-3-beta-D-galactosyl-sn-glycerol + D-Galactose D-Gal alpha 1->6D-Gal alpha 1->6D-Glucose + Water <> D-Galactose + Melibiose Water + Globotriaosylceramide <> D-Galactose + Lactosylceramide Melibiose + Water <> D-Galactose + D-Glucose Lactose + Water <> D-Glucose + D-Galactose D-Galactose + NAD 3-keto-β-D-galactose + NADH + Hydrogen ion Adenosine triphosphate + D-Galactose + Water > ADP + Phosphate + D-Galactose + Hydrogen ion More...Adenosine triphosphate + D-Galactose + Water > ADP + Phosphate + D-Galactose + Hydrogen ion D-Galactose <> D-Galactose D-Galactose <> D-Galactose Water + Melibiose > D-Galactose + b-D-Glucose Water + alpha-Lactose > D-Galactose + b-D-Glucose D-Galactose + Adenosine triphosphate > Hydrogen ion + Galactose 1-phosphate + ADP Adenosine triphosphate + D-Galactose > ADP + Galactose 1-phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Avigad, Gad. Synthesis of D-galactose-6-t and D-galactosides-6-t. Carbohydrate Research (1967), 3(4), 430-4. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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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 hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids
- Gene Name:
- melA
- Uniprot ID:
- P06720
- Molecular weight:
- 50657
Reactions
| Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids. |
- General function:
- Involved in beta-galactosidase activity
- Specific function:
- The wild-type enzyme is an ineffective lactase. Two classes of point mutations dramatically improve activity of the enzyme
- Gene Name:
- ebgA
- Uniprot ID:
- P06864
- Molecular weight:
- 117878
Reactions
| Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides. |
- General function:
- Involved in galactokinase activity
- Specific function:
- ATP + D-galactose = ADP + alpha-D-galactose 1- phosphate
- Gene Name:
- galK
- Uniprot ID:
- P0A6T3
- Molecular weight:
- 41442
Reactions
| ATP + D-galactose = ADP + alpha-D-galactose 1-phosphate. |
- 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:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex MglABC involved in galactose/methyl galactoside import. Responsible for energy coupling to the transport system (Probable)
- Gene Name:
- mglA
- Uniprot ID:
- P0AAG8
- Molecular weight:
- 56415
Reactions
| ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In). |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Absolutely required for the growth of E.coli in a high- phosphate medium containing G-1-P as the sole carbon source
- Gene Name:
- agp
- Uniprot ID:
- P19926
- Molecular weight:
- 45683
Reactions
| Alpha-D-glucose 1-phosphate + H(2)O = D-glucose + phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Hydrolysis of terminal, non-reducing beta-D- glucosyl residues with release of beta-D-glucose
- Gene Name:
- bglX
- Uniprot ID:
- P33363
- Molecular weight:
- 83459
Reactions
| Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Specific function unknown
- Gene Name:
- ytfR
- Uniprot ID:
- Q6BEX0
- Molecular weight:
- 55259
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yjfF
- Uniprot ID:
- P37772
- Molecular weight:
- 34977
- 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:
- Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ytfT
- Uniprot ID:
- P39328
- Molecular weight:
- 35659
- 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 transferase activity
- Specific function:
- Specific function unknown
- Gene Name:
- wcaK
- Uniprot ID:
- P71242
- Molecular weight:
- 47343
- General function:
- Carbohydrate transport and metabolism
- Specific function:
- This protein is involved in the active transport of galactose and glucose. It plays a role in the chemotaxis towards the two sugars by interacting with the trg chemoreceptor
- Gene Name:
- mglB
- Uniprot ID:
- P0AEE5
- Molecular weight:
- 35712
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- ebgC
- Uniprot ID:
- P0AC73
- Molecular weight:
- Not Available
- General function:
- carbohydrate metabolic process
- Specific function:
- Not Available
- Gene Name:
- lacZ
- Uniprot ID:
- G0ZKW2
- Molecular weight:
- 116482
Reactions
| = |
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex MglABC involved in galactose/methyl galactoside import. Responsible for energy coupling to the transport system (Probable)
- Gene Name:
- mglA
- Uniprot ID:
- P0AAG8
- Molecular weight:
- 56415
Reactions
| ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In). |
- General function:
- Involved in nucleotide binding
- Specific function:
- Specific function unknown
- Gene Name:
- ytfR
- Uniprot ID:
- Q6BEX0
- Molecular weight:
- 55259
- General function:
- Involved in transmembrane transporter activity
- Specific function:
- Uptake of galactose across the boundary membrane with the concomitant transport of protons into the cell (symport system)
- Gene Name:
- galP
- Uniprot ID:
- P0AEP1
- Molecular weight:
- 50982
- 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:
- Involved in transporter activity
- Specific function:
- Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yjfF
- Uniprot ID:
- P37772
- Molecular weight:
- 34977
- 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:
- Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- ytfT
- Uniprot ID:
- P39328
- Molecular weight:
- 35659
- 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:
- Carbohydrate transport and metabolism
- Specific function:
- This protein is involved in the active transport of galactose and glucose. It plays a role in the chemotaxis towards the two sugars by interacting with the trg chemoreceptor
- Gene Name:
- mglB
- Uniprot ID:
- P0AEE5
- Molecular weight:
- 35712
- 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