D-Maltose (ECMDB00163) (M2MDB000065)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:22:31 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | D-Maltose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Maltose, or malt sugar, is a disaccharide formed from two units of glucose joined with an alpha (1->4) linkage. It is the second member of an important biochemical series of glucose chains. The addition of another glucose unit yields maltotriose, Further additions will produce dextrins, also called maltodextrins, and eventually starch. Maltose can be broken down into two glucose molecules by hydrolysis in living organisms. (PMID: 14522745) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C12H22O11 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 342.2965 Monoisotopic: 342.116211546 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | GUBGYTABKSRVRQ-DKBJLJRDSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 69-79-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 102-103 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | ADP + Phosphate + 4 Hydrogen ion + Heme + Nickel(2+) + Iron chelate + Taurine + Molybdate + Magnesium + Fe3+ + Potassium + Polyamine + vitamin B12 + Sulfate + glycerol-3-phosphate + Phosphonate + D-Maltose <> Adenosine triphosphate +3 Hydrogen ion + Water Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acid Adenosine triphosphate + Water + D-Maltose > ADP + Hydrogen ion + D-Maltose + Phosphate Adenosine triphosphate + Water + D-Maltose > ADP + Hydrogen ion + D-Maltose + Phosphate Water + Maltotriose > D-Glucose + D-Maltose Acetyl-CoA + D-Maltose <> Acetyl-maltose + Coenzyme A D-Maltose + Maltotriose > D-Glucose + Maltotetraose D-Maltose + Maltotetraose > D-Glucose + Maltopentaose D-Maltose + Maltohexaose > D-Glucose + Maltoheptaose D-Maltose + Maltopentaose > D-Glucose + Maltohexaose D-Maltose + Water <>2 alpha-D-Glucose Protein N(pi)-phospho-L-histidine + D-Maltose <> Protein histidine + Maltose 6'-phosphate 1,4-alpha-D-glucan + D-Glucose <> D-Maltose Adenosine triphosphate + D-Maltose + Water > ADP + Phosphate + D-Maltose + Hydrogen ion Adenosine triphosphate + D-Maltose + Water > ADP + Phosphate + D-Maltose + Hydrogen ion Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose Maltotriose + Water > D-Maltose + D-Glucose Acetyl-CoA + D-Maltose > CoA + Acetyl-maltose Adenosine triphosphate + Water + D-Maltose > ADP + Inorganic phosphate + D-Maltose Adenosine triphosphate + Water + D-Maltose > ADP + Inorganic phosphate + D-Maltose D-Maltose + Adenosine triphosphate + Water > D-Maltose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP D-Maltose + Adenosine triphosphate + Water > D-Maltose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | Pedersen, Sven; Vang Hendriksen, Hanne. Method for production of maltose and/or enzymatically modified starch. PCT Int. Appl. (2001), 99 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring phosphorus-containing groups
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
- Gene Name:
- ptsI
- Uniprot ID:
- P08839
- Molecular weight:
- 63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine. |
- General function:
- Involved in 4-alpha-glucanotransferase activity
- Specific function:
- Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan
- Gene Name:
- malQ
- Uniprot ID:
- P15977
- Molecular weight:
- 78503
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan. |
- General function:
- Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
- Specific function:
- MalX encodes a phosphotransferase system enzyme II that can recognize glucose and maltose as substrates even though these sugars may not represent the natural substrates of the system
- Gene Name:
- malX
- Uniprot ID:
- P19642
- Molecular weight:
- 56627
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- May play a role in regulating the intracellular level of maltotriose. Cleaves glucose from the reducing end of maltotriose and longer maltodextrins with a chain length of up to 7 glucose units
- Gene Name:
- malZ
- Uniprot ID:
- P21517
- Molecular weight:
- 69172
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose. |
- General function:
- Involved in catalytic activity
- Specific function:
- Exhibits hydrolysis activity against alpha-glucosyl fluoride, although natural substrates, such as alpha-glucobioses are scarcely hydrolyzed
- Gene Name:
- yihQ
- Uniprot ID:
- P32138
- Molecular weight:
- 77274
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
- Gene Name:
- malK
- Uniprot ID:
- P68187
- Molecular weight:
- 40990
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In). |
- General function:
- Involved in sugar:hydrogen symporter activity
- Specific function:
- The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
- Gene Name:
- crr
- Uniprot ID:
- P69783
- Molecular weight:
- 18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine. |
- General function:
- Involved in transferase activity
- Specific function:
- Acetylates maltose and other sugars
- Gene Name:
- maa
- Uniprot ID:
- P77791
- Molecular weight:
- 20096
Reactions
Acetyl-CoA + maltose = CoA + acetyl-maltose. |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malF
- Uniprot ID:
- P02916
- Molecular weight:
- 57013
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malG
- Uniprot ID:
- P68183
- Molecular weight:
- 32225
- General function:
- Involved in maltose transmembrane transporter activity
- Specific function:
- Involved in the high-affinity maltose membrane transport system malEFGK. Initial receptor for the active transport of and chemotaxis toward maltooligosaccharides
- Gene Name:
- malE
- Uniprot ID:
- P0AEX9
- Molecular weight:
- 43387
- General function:
- Involved in sugar:hydrogen symporter activity
- Specific function:
- General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
- Gene Name:
- ptsH
- Uniprot ID:
- P0AA04
- Molecular weight:
- 9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine. |
Transporters
- General function:
- Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
- Specific function:
- MalX encodes a phosphotransferase system enzyme II that can recognize glucose and maltose as substrates even though these sugars may not represent the natural substrates of the system
- Gene Name:
- malX
- Uniprot ID:
- P19642
- Molecular weight:
- 56627
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate. |
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
- Gene Name:
- malK
- Uniprot ID:
- P68187
- Molecular weight:
- 40990
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malF
- Uniprot ID:
- P02916
- Molecular weight:
- 57013
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- malG
- Uniprot ID:
- P68183
- Molecular weight:
- 32225
- General function:
- Involved in maltose transmembrane transporter activity
- Specific function:
- Involved in the high-affinity maltose membrane transport system malEFGK. Initial receptor for the active transport of and chemotaxis toward maltooligosaccharides
- Gene Name:
- malE
- Uniprot ID:
- P0AEX9
- Molecular weight:
- 43387
- General function:
- Involved in porin activity
- Specific function:
- Involved in the transport of maltose and maltodextrins, indispensable for translocation of dextrins containing more than three glucosyl moieties. A hydrophobic path ("greasy slide") of aromatic residues serves to guide and select the sugars for transport through the channel. Also acts as a receptor for several bacteriophages including lambda
- Gene Name:
- lamB
- Uniprot ID:
- P02943
- Molecular weight:
- 49912