Record Information
Version2.0
Creation Date2012-07-30 14:55:05 -0600
Update Date2015-06-03 17:20:59 -0600
Secondary Accession Numbers
  • ECMDB21243
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
Thumb
Synonyms:
  • a-D-GLCP-(1RIght4)-a-D-GLCP-(1Right4)-a-D-GLCP-(1Right4)-a-D-GLCP-(1Right4)-a-D-GLCP-(1Right4)-D-GLC
  • a-D-Glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-D-glucose
  • Alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-D-Glc
  • Alpha-D-Glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-D-glucose
  • Maltohexanose DP6
  • Maltohexaose
  • α-D-GLCP-(1RIght4)-α-D-GLCP-(1Right4)-α-D-GLCP-(1Right4)-α-D-GLCP-(1Right4)-α-D-GLCP-(1Right4)-D-GLC
  • α-D-Glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-D-glucose
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
DescriptionThis compound belongs to the class of chemical entities known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility252.0 mg/mLALOGPS
logP-2.5ALOGPS
logP-12ChemAxon
logS-0.6ALOGPS
pKa (Strongest Acidic)11.15ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area506.13 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity197.99 m3·mol-1ChemAxon
Polarizability92.31 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03kj-0504436069-81527007ed999f98a213View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gv-0809647062-d050e9c757955d7b5830View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gl-0906223021-223dd1e9a27601280e19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0210212029-e287313027c8a634a1ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0412213029-23721df364097afc42fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-1926022112-e7385ad76fe827245a6eView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27445
HMDB IDHMDB12253
Pubchem Compound ID439606
Kegg IDC01936
ChemSpider ID388684
Wikipedia IDNot Available
BioCyc IDMALTOHEXAOSE
EcoCyc IDMALTOHEXAOSE

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