Record Information
Version2.0
Creation Date2012-07-30 14:55:05 -0600
Update Date2015-06-03 17:20:59 -0600
Secondary Accession Numbers
  • ECMDB21244
Identification
Name:Maltopentaose
DescriptionMaltopentaose is pentasaccaride or more specifically a pentasaccharide comprised of five D-glucose residues connected by alpha(1->4) linkages. It is a substrate for energy metabolism and carbon for E. coli. Maltopentaose 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)-D-GLC
  • 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)-D-Glc
  • Alpha-D-Glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-D-glucose
  • 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)-D-glucose
Chemical Formula:C27H48O26
Weight:Average: 788.6544
Monoisotopic: 788.243381708
InChI Key:JAEVVUVBPPQABG-UHFFFAOYSA-N
InChI:InChI=1S/C27H48O26/c28-1-5(32)8(33)23(45-4-31)53-25-16(41)11(36)19(7(3-30)47-25)49-27-17(42)12(37)20(22(44)52-27)50-24-15(40)10(35)18(6(2-29)46-24)48-26-14(39)9(34)13(38)21(43)51-26/h5-44H,1-4H2
CAS number:34620-76-3
IUPAC Name:6-({6-[(6-{[4,5-dihydroxy-2-(hydroxymethyl)-6-[2,3,4-trihydroxy-1-(hydroxymethoxy)butoxy]oxan-3-yl]oxy}-2,4,5-trihydroxyoxan-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxy)oxane-2,3,4,5-tetrol
Traditional IUPAC Name:6-({6-[(6-{[4,5-dihydroxy-2-(hydroxymethyl)-6-[2,3,4-trihydroxy-1-(hydroxymethoxy)butoxy]oxan-3-yl]oxy}-2,4,5-trihydroxyoxan-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxy)oxane-2,3,4,5-tetrol
SMILES:OCOC(OC1OC(CO)C(OC2OC(O)C(OC3OC(CO)C(OC4OC(O)C(O)C(O)C4O)C(O)C3O)C(O)C2O)C(O)C1O)C(O)C(O)CO
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty acyl
  • 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 Solubility222 g/LALOGPS
logP-2.4ALOGPS
logP-9.3ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)10.89ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area426.98 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity153.15 m³·mol⁻¹ChemAxon
Polarizability72.78 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-00di-5915508800-72f2c791ff202b0e61ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ka-9808504100-6d0970d33d0af715b357View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-4906402100-2f9197699db34da82a13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-9202103500-7dde14354b2a9eb056c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-9706202500-0bff88fde726e717e7c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9737100000-f02b4799d7b5f18dfb46View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID62006
HMDB IDHMDB12254
Pubchem Compound ID124005
Kegg IDNot Available
ChemSpider ID21229918
Wikipedia IDNot Available
BioCyc IDMALTOPENTAOSE
EcoCyc IDMALTOPENTAOSE

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 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