Record Information
Version2.0
Creation Date2012-05-31 13:49:19 -0600
Update Date2015-09-13 15:15:22 -0600
Secondary Accession Numbers
  • ECMDB01296
Identification
Name:Maltotetraose
Description:Maltotetraose is a member of the chemical class known as Tetrahexoses. These are tetrasaccharides containing four hexose carbohydrates. Maltotetraose is invovled in Glycerol degradation. r 15;80(8):2939-48.)
Structure
Thumb
Synonyms:
  • a-1,4-Tetraglucose
  • Alpha-1,4-Tetraglucose
  • Amylotetraose
  • Maltotetraose
  • Maltotetraose (6CI,8CI)
  • O-a-D-Glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-D-glucose
  • O-a-D-Glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-O-a-D-glucopyranosyl-(1-4)-D-glucose (9ci)
  • O-a-D-Glucopyranosyl-(1->4)-O(4XI)-a-D-xylo-hexopyranosyl-(1->4)-O-a-D-glucopyranosyl-(1->4)-D-glucose
  • O-a-D-Glucopyranosyl-(1.4)-O-a-D-glucopyranosyl-(1.4)-O-a-D-glucopyranosyl-(1.4)-D-glucose
  • O-a-delta-Glucopyranosyl-(1-4)-O-a-delta-glucopyranosyl-(1-4)-O-a-delta-glucopyranosyl-(1-4)-delta-glucose
  • O-a-delta-Glucopyranosyl-(1->4)-O(4XI)-a-delta-xylo-hexopyranosyl-(1->4)-O-a-delta-glucopyranosyl-(1->4)-delta-glucose
  • O-a-delta-Glucopyranosyl-(1.4)-O-a-delta-glucopyranosyl-(1.4)-O-a-delta-glucopyranosyl-(1.4)-delta-glucose
  • O-a-δ-Glucopyranosyl-(1-4)-O-a-δ-glucopyranosyl-(1-4)-O-a-δ-glucopyranosyl-(1-4)-δ-glucose
  • O-a-δ-Glucopyranosyl-(1->4)-O(4xi)-a-δ-xylo-hexopyranosyl-(1->4)-O-a-δ-glucopyranosyl-(1->4)-δ-glucose
  • O-a-δ-Glucopyranosyl-(1.4)-O-a-δ-glucopyranosyl-(1.4)-O-a-δ-glucopyranosyl-(1.4)-δ-glucose
  • O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-Glucose
  • O-alpha-D-Glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-Glucose (9CI)
  • O-alpha-D-Glucopyranosyl-(1->4)-O(4xi)-alpha-D-xylo-hexopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4)-D-glucose
  • O-alpha-D-Glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-D-glucose
  • O-alpha-delta-glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-delta-Glucose
  • O-alpha-delta-glucopyranosyl-(1->4)-O(4xi)-alpha-delta-xylo-hexopyranosyl-(1->4)-O-alpha-delta-glucopyranosyl-(1->4)-delta-glucose
  • O-alpha-delta-Glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-delta-glucose
  • O-α-D-Glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-D-glucose
  • O-α-D-Glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-O-α-D-glucopyranosyl-(1-4)-D-glucose (9ci)
  • O-α-D-Glucopyranosyl-(1->4)-O(4XI)-α-D-xylo-hexopyranosyl-(1->4)-O-α-D-glucopyranosyl-(1->4)-D-glucose
  • O-α-D-Glucopyranosyl-(1.4)-O-α-D-glucopyranosyl-(1.4)-O-α-D-glucopyranosyl-(1.4)-D-glucose
  • O-α-δ-Glucopyranosyl-(1-4)-O-α-δ-glucopyranosyl-(1-4)-O-α-δ-glucopyranosyl-(1-4)-δ-glucose
  • O-α-δ-Glucopyranosyl-(1->4)-O(4XI)-α-δ-xylo-hexopyranosyl-(1->4)-O-α-δ-glucopyranosyl-(1->4)-δ-glucose
  • O-α-δ-Glucopyranosyl-(1.4)-O-α-δ-glucopyranosyl-(1.4)-O-α-δ-glucopyranosyl-(1.4)-δ-glucose
  • α-1,4-Tetraglucose
Chemical Formula:C24H42O21
Weight:Average: 666.5777
Monoisotopic: 666.221858406
InChI Key:LUEWUZLMQUOBSB-AYQJAVFRSA-N
InChI:InChI=1S/C24H42O21/c25-1-5-9(29)10(30)15(35)22(40-5)44-19-7(3-27)42-24(17(37)12(19)32)45-20-8(4-28)41-23(16(36)13(20)33)43-18-6(2-26)39-21(38)14(34)11(18)31/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21?,22-,23-,24-/m1/s1
CAS number:34612-38-9
IUPAC Name:(2R,3R,4S,5S,6R)-2-{[(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}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional IUPAC Name:(2R,3R,4S,5S,6R)-2-{[(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}-6-(hydroxymethyl)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[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)C(O)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
LogP:-10.139PhysProp
Predicted Properties
PropertyValueSource
Water Solubility350.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-8.2ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)11.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area347.83 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.16 m3·mol-1ChemAxon
Polarizability62.18 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Starch and sucrose metabolismPW000941 Pw000941Pw000941 greyscalePw000941 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-052s-2321309000-339e4ce9a5b6b7184b25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-002r-0109714000-92449118dd9f88ced9e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0902000000-bada4f81875480cef630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03ds-4900000000-8c70af31defdcfbbdaceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002n-0509528000-5fd5603d944802261099View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003l-0609511000-93559566aadd9ddb01d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01sl-0904101000-2dc209564506d51c072bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0322229000-836fde463c0313bb06f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bm-2925316000-9af8644e1895bb3e5446View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-2934001000-a30993c2dc002a86ef84View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • An Y, Young SP, Kishnani PS, Millington DS, Amalfitano A, Corz D, Chen YT: Glucose tetrasaccharide as a biomarker for monitoring the therapeutic response to enzyme replacement therapy for Pompe disease. Mol Genet Metab. 2005 Aug;85(4):247-54. Pubmed: 15886040
  • Dewit O, Dibba B, Prentice A: Breast-milk amylase activity in English and Gambian mothers: effects of prolonged lactation, maternal parity, and individual variations. Pediatr Res. 1990 Nov;28(5):502-6. Pubmed: 1701531
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kuriyama M, Hiwatari R, Osame M, Igata A: Leucocyte alpha-1,4- and alpha-1,6-glucosidase activities towards oligosaccharides in late onset glycogenosis type II. Tohoku J Exp Med. 1990 Aug;161(4):343-51. Pubmed: 2256108
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Whitlow KJ, Gochman N, Forrester RL, Wataji LJ: Maltotetraose as a substrate for enzyme-coupled assay of amylase activity in serum and urine. Clin Chem. 1979 Mar;25(3):481-3. Pubmed: 95558
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yuge O, Morio M, Fukui T, Fujii K, Kikuchi H, Takahashi S: Maltotriose and maltotetraose excreted in urine following intravenous administration of maltose to human volunteers. Jpn J Surg. 1983 Jul;13(4):296-303. Pubmed: 6645121
Synthesis Reference:Zhu, Ming. Production of maltotetraose. Wuxi Qinggong Daxue Xuebao (1999), 18(2), 7-12.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID61988
HMDB IDHMDB01296
Pubchem Compound ID439639
Kegg IDC02052
ChemSpider ID388711
Wikipedia IDNot Available
BioCyc IDMALTOTETRAOSE
EcoCyc IDMALTOTETRAOSE

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 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 catalytic activity
Specific function:
Hydrolyzes the alpha-1,6-glucosidic linkages in glycogen which has first been partially depolymerized by phosphorylase. Shows only very little activity with native glycogen
Gene Name:
glgX
Uniprot ID:
P15067
Molecular weight:
73576

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