Maltohexaose (ECMDB21243) (M2MDB001651)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-07-30 14:55:05 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-06-03 17:20:59 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Maltohexaose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Maltohexaose is hexasaccaride or more specifically a hexasaccharide comprised of six D-glucose residues connected by alpha(1->4) linkages. It is a substrate for energy metabolism and carbon for E. coli. Maltohexaose is imported into the cell via the maltooligosaccharide-specific LamB-channel of Escherichia coli (also called maltoporin). It is degraded by alpha amylase. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C36H62O31 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 990.8589 Monoisotopic: 990.327505266 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | OCIBBXPLUVYKCH-LIGGPISVSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C36H62O31/c37-1-7-13(43)14(44)21(51)32(58-7)64-27-9(3-39)60-34(23(53)16(27)46)66-29-11(5-41)62-36(25(55)18(29)48)67-30-12(6-42)61-35(24(54)19(30)49)65-28-10(4-40)59-33(22(52)17(28)47)63-26-8(2-38)57-31(56)20(50)15(26)45/h7-56H,1-6H2/t7-,8-,9-,10-,11-,12-,13-,14+,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31?,32-,33-,34-,35-,36-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 34620-77-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | maltohexaose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)C(O)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO)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 oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic oxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Organooxygen compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Carbohydrates and carbohydrate conjugates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Oligosaccharides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Adenosine triphosphate + Water + Maltohexaose > ADP + Hydrogen ion + Maltohexaose + Phosphate Adenosine triphosphate + Water + Maltohexaose > ADP + Hydrogen ion + Maltohexaose + Phosphate Water + Maltoheptaose > D-Glucose + Maltohexaose Water + Maltohexaose > D-Glucose + Maltopentaose 1,4-alpha-D-glucan > Maltohexaose D-Maltose + Maltohexaose > D-Glucose + Maltoheptaose D-Maltose + Maltopentaose > D-Glucose + Maltohexaose Maltoheptaose + Phosphate <> Glucose 1-phosphate + Maltohexaose Maltohexaose + Phosphate <> Glucose 1-phosphate + Maltopentaose a 1,4-α-D-glucan + Water > a 1,4-α-D-glucan + Maltohexaose | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: |
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| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in phosphorylase activity
- Specific function:
- Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
- Gene Name:
- malP
- Uniprot ID:
- P00490
- Molecular weight:
- 90522
Reactions
| (1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate. |
- 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 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:
- Since only maltooligosaccharides up to a chain length of 6 glucose units are actively transported through the cytoplasmic membrane via the membrane-bound complex of three proteins, malF, malG, and malK, longer maltooligosaccharides must first be degraded by the periplasmic alpha-amylase, the malS protein
- Gene Name:
- malS
- Uniprot ID:
- P25718
- Molecular weight:
- 75712
Reactions
| Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units. |
- General function:
- Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
- Specific function:
- Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in oligosaccharides and polysaccharides
- Gene Name:
- amyA
- Uniprot ID:
- P26612
- Molecular weight:
- 56639
Reactions
| Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units. |
- 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
Transporters
- 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