Maltotetraose (PAMDB000327)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000327
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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 666.5777
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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 ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassOligosaccharides
Direct Parent Oligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not 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:
Adenosine triphosphate + Water + Maltotetraose > ADP + Hydrogen ion + Maltotetraose + Phosphate
Adenosine triphosphate + Water + Maltotetraose > ADP + Hydrogen ion + Maltotetraose + Phosphate
Water + Maltotetraose > D-Glucose + Maltotriose
Water + Maltopentaose > D-Glucose + Maltotetraose
D-Maltose + Maltotriose > D-Glucose + Maltotetraose
D-Maltose + Maltotetraose > D-Glucose + Maltopentaose
Maltopentaose + Phosphate <> Glucose 1-phosphate + Maltotetraose
Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose
a limit dextrin + Water > a debranched limit dextrin + Maltotetraose
Maltotetraose + Phosphate <> Maltotriose + Glucose 1-phosphate
-->-->Maltotetraose + Phosphate > Maltotriose + Alpha-D-glucose 1-phosphate
Dextrin + Water + Dextrin > debranched limit dextrin + Maltotetraose
Maltotetraose + Adenosine triphosphate + Water > Maltotetraose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP
Maltotetraose + Adenosine triphosphate + Water > Maltotetraose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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

Protein Details
• Maltose/maltodextrin import ATP-binding protein MalK
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
Locus Tag:
PA2341
Molecular weight:
40.2 kDa
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).

Transporters

Protein Details
• Maltose/maltodextrin import ATP-binding protein MalK
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
Locus Tag:
PA2341
Molecular weight:
40.2 kDa
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).