D-Maltose (PAMDB000065)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000065
Identification
Name: D-Maltose
Description:Maltose, or malt sugar, is a disaccharide formed from two units of glucose joined with an alpha (1->4) linkage. It is the second member of an important biochemical series of glucose chains. The addition of another glucose unit yields maltotriose, Further additions will produce dextrins, also called maltodextrins, and eventually starch. Maltose can be broken down into two glucose molecules by hydrolysis in living organisms.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-a-D-Glucopyranosyl-4-a-D-glucopyranose
  • 1-a-delta-Glucopyranosyl-4-a-delta-glucopyranose
  • 1-a-δ-Glucopyranosyl-4-a-δ-glucopyranose
  • 1-alpha-D-Glucopyranosyl-4-alpha-D-glucopyranose
  • 1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose
  • 1-α-D-Glucopyranosyl-4-α-D-glucopyranose
  • 1-α-δ-Glucopyranosyl-4-α-δ-glucopyranose
  • 4-(a-D-glucopyranosido)-a-Glucopyranose
  • 4-(a-D-glucosido)-D-Glucose
  • 4-(a-delta-glucopyranosido)-a-Glucopyranose
  • 4-(a-delta-glucosido)-delta-Glucose
  • 4-(a-δ-glucopyranosido)-a-Glucopyranose
  • 4-(a-δ-glucosido)-δ-Glucose
  • 4-(alpha-D-Glucopyranosido)-alpha-glucopyranose
  • 4-(alpha-D-Glucosido)-D-glucose
  • 4-(alpha-delta-Glucopyranosido)-alpha-glucopyranose
  • 4-(alpha-delta-Glucosido)-delta-glucose
  • 4-(α-D-glucopyranosido)-α-Glucopyranose
  • 4-(α-D-glucosido)-D-Glucose
  • 4-(α-δ-glucopyranosido)-α-Glucopyranose
  • 4-(α-δ-glucosido)-δ-Glucose
  • 4-O-a-D-Glucopyranosyl-D-glucopyranose
  • 4-O-a-D-Glucopyranosyl-D-glucose
  • 4-O-a-delta-Glucopyranosyl-delta-glucopyranose
  • 4-O-a-delta-Glucopyranosyl-delta-glucose
  • 4-O-a-δ-Glucopyranosyl-δ-glucopyranose
  • 4-O-a-δ-Glucopyranosyl-δ-glucose
  • 4-O-alpha-D-Glucopyranosyl-D-glucopyranose
  • 4-O-alpha-D-Glucopyranosyl-D-glucose
  • 4-O-alpha-delta-Glucopyranosyl-delta-glucopyranose
  • 4-O-alpha-delta-Glucopyranosyl-delta-glucose
  • 4-O-α-D-Glucopyranosyl-D-glucopyranose
  • 4-O-α-D-Glucopyranosyl-D-glucose
  • 4-O-α-δ-Glucopyranosyl-δ-glucopyranose
  • 4-O-α-δ-Glucopyranosyl-δ-glucose
  • a-D-GLCP-(1->4)-D-GLCP
  • a-D-Glucopyranosyl-(1->4)-D-glucopyranose
  • a-D-Glucopyranosyl-(1->4)-D-glucose
  • a-delta-GLCP-(1->4)-delta-GLCP
  • a-delta-Glucopyranosyl-(1->4)-delta-glucopyranose
  • a-delta-Glucopyranosyl-(1->4)-delta-glucose
  • a-Malt sugar
  • a-δ-GLCP-(1->4)-δ-GLCP
  • a-δ-Glucopyranosyl-(1->4)-δ-glucopyranose
  • a-δ-Glucopyranosyl-(1->4)-δ-glucose
  • Advantose 100
  • Alpha-D-Glcp-(1->4)-D-Glcp
  • Alpha-D-Glucopyranosyl-(1->4)-D-glucopyranose
  • Alpha-D-Glucopyranosyl-(1->4)-D-glucose
  • Alpha-delta-Glcp-(1->4)-delta-Glcp
  • Alpha-delta-Glucopyranosyl-(1->4)-delta-glucopyranose
  • Alpha-delta-Glucopyranosyl-(1->4)-delta-glucose
  • Alpha-Malt sugar
  • Cextromaltose
  • D-(+)-Maltose
  • D-Maltose
  • Delta-(+)-Maltose
  • Delta-Maltose
  • Finetose
  • Finetose F
  • Madoros
  • Madoros (TN)
  • Malt sugar
  • Maltobiose
  • Maltodiose
  • Maltos
  • Maltose
  • Maltose HH
  • Maltose HHH
  • Maltose solution
  • Malzzucker
  • Martos-10
  • Sunmalt
  • Sunmalt S
  • α-D-GLCP-(1->4)-D-GLCP
  • α-D-Glucopyranosyl-(1->4)-D-glucopyranose
  • α-D-Glucopyranosyl-(1->4)-D-glucose
  • α-Malt sugar
  • α-δ-GLCP-(1->4)-δ-GLCP
  • α-δ-Glucopyranosyl-(1->4)-δ-glucopyranose
  • α-δ-Glucopyranosyl-(1->4)-δ-glucose
  • δ-(+)-Maltose
  • δ-Maltose
Chemical Formula: C12H22O11
Average Molecular Weight: 342.2965
Monoisotopic Molecular Weight: 342.116211546
InChI Key: GUBGYTABKSRVRQ-DKBJLJRDSA-N
InChI:InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1
CAS number: 69-79-4
IUPAC Name:(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
Traditional IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}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)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 o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent O-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • 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
Physical Properties
State: Solid
Charge:0
Melting point: 102-103 °C
Experimental Properties:
PropertyValueSource
Water Solubility:780.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility586.0 mg/mLALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)11.25ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m3·mol-1ChemAxon
Polarizability31.43 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acid
Adenosine triphosphate + Water + D-Maltose > ADP + Hydrogen ion + D-Maltose + Phosphate
Adenosine triphosphate + Water + D-Maltose > ADP + Hydrogen ion + D-Maltose + Phosphate
Acetyl-CoA + D-Maltose <> Acetyl-maltose + Coenzyme A
D-Maltose + Maltotriose > D-Glucose + Maltotetraose
D-Maltose + Maltotetraose > D-Glucose + Maltopentaose
D-Maltose + Maltohexaose > D-Glucose + Maltoheptaose
D-Maltose + Maltopentaose > D-Glucose + Maltohexaose
D-Maltose + Water <>2 alpha-D-Glucose
Protein N(pi)-phospho-L-histidine + D-Maltose <> Protein histidine + Maltose 6'-phosphate
1,4-alpha-D-glucan + D-Glucose <> D-Maltose
-->-->Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose
Maltotriose + Water > D-Maltose + D-Glucose
Adenosine triphosphate + Water + D-Maltose > ADP + Inorganic phosphate + D-Maltose
Adenosine triphosphate + Water + D-Maltose > ADP + Inorganic phosphate + D-Maltose
D-Maltose + Adenosine triphosphate + Water > D-Maltose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP
D-Maltose + Adenosine triphosphate + Water > D-Maltose + Phosphate + Hydrogen ion + Adenosine diphosphate + ADP
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0149000000-74748828832d87932342View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-008c-2950000000-4ebee22b86c2cc9ee3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kg-9710000000-041dbc580f99b8881518View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Andrews RK, Suzuki-Inoue K, Shen Y, Tulasne D, Watson SP, Berndt MC: Interaction of calmodulin with the cytoplasmic domain of platelet glycoprotein VI. Blood. 2002 Jun 1;99(11):4219-21. Pubmed: 12010829
  • Chiba S, Hiromi K, Minamiura N, Ohnishi M, Shimomura T, Suga K, Suganuma T, Tanaka A, Tomioka S, Yamamoto T: Quantitative study on anomeric forms of glucose produced by alpha-glucosidases. J Biochem (Tokyo). 1979 May;85(5):1135-41. Pubmed: 376499
  • Daly JJ, Sherman JK, Green L, Hostetler TL: Survival of Trichomonas vaginalis in human semen. Genitourin Med. 1989 Apr;65(2):106-8. Pubmed: 2787774
  • Dorner KM: Quantitative determination of lactose, maltose, and sucrose in urine. Eur J Pediatr. 1977 Aug 23;126(1-2):45-52. Pubmed: 902663
  • Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. Pubmed: 3275321
  • Janoshazi A, Solomon AK: Initial steps of alpha- and beta-D-glucose binding to intact red cell membrane. J Membr Biol. 1993 Mar;132(2):167-78. Pubmed: 8496948
  • 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
  • Leth-Larsen R, Holmskov U, Hojrup P: Structural characterization of human and bovine lung surfactant protein D. Biochem J. 1999 Nov 1;343 Pt 3:645-52. Pubmed: 10527944
  • Lingstrom P, Birkhed D, Granfeldt Y, Bjorck I: pH measurements of human dental plaque after consumption of starchy foods using the microtouch and the sampling method. Caries Res. 1993;27(5):394-401. Pubmed: 8242677
  • Lu J, Willis AC, Reid KB: Purification, characterization and cDNA cloning of human lung surfactant protein D. Biochem J. 1992 Jun 15;284 ( Pt 3):795-802. Pubmed: 1339284
  • McCue JP, Hein RH, Tenold R: Three generations of immunoglobulin G preparations for clinical use. Rev Infect Dis. 1986 Jul-Aug;8 Suppl 4:S374-81. Pubmed: 3092303
  • Miller LJ, Malagelada JR, Taylor WF, Go VL: Intestinal control of human postprandial gastric function: the role of components of jejunoileal chyme in regulating gastric secretion and gastric emptying. Gastroenterology. 1981 Apr;80(4):763-9. Pubmed: 7202948
  • Morse DR, Schacterle GR, Furst L, Zaydenberg M, Pollack RL: Oral digestion of a complex-carbohydrate cereal: effects of stress and relaxation on physiological and salivary measures. Am J Clin Nutr. 1989 Jan;49(1):97-105. Pubmed: 2463752
  • Roy E, Stavropoulos E, Brennan J, Coade S, Grigorieva E, Walker B, Dagg B, Tascon RE, Lowrie DB, Colston MJ, Jolles S: Therapeutic efficacy of high-dose intravenous immunoglobulin in Mycobacterium tuberculosis infection in mice. Infect Immun. 2005 Sep;73(9):6101-9. Pubmed: 16113331
  • Rubaltelli FF, Biadaioli R, Pecile P, Nicoletti P: Intestinal flora in breast- and bottle-fed infants. J Perinat Med. 1998;26(3):186-91. Pubmed: 9773376
  • Sherman JK, Hostetler TL, McHenry K, Daly JJ: Cryosurvival of Trichomonas vaginalis during cryopreservation of human semen. Cryobiology. 1991 Jun;28(3):246-50. Pubmed: 1864083
  • Sigman-Grant, M., Morita, J. (2003). "Defining and interpreting intakes of sugars." Am J Clin Nutr 78:815S-826S. Pubmed: 14522745
  • Tiwari F, Singh DK: Behavioural responses of the snail Lymnaea acuminata to carbohydrates in snail-attractant pellets. Naturwissenschaften. 2004 Aug;91(8):378-80. Epub 2004 Jun 2. Pubmed: 15309310
  • 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
  • van Leeuwen L: New saccharogenic determination of alpha-amylase in serum and urine. Clin Chem. 1979 Feb;25(2):215-7. Pubmed: 215341
  • 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
  • Wyss C, Choi BK, Schupbach P, Guggenheim B, Gobel UB: Treponema maltophilum sp. nov., a small oral spirochete isolated from human periodontal lesions. Int J Syst Bacteriol. 1996 Jul;46(3):745-52. Pubmed: 8782684
  • Yamamoto T, Kajiura S, Hirai Y, Watanabe T: Capnocytophaga haemolytica sp. nov. and Capnocytophaga granulosa sp. nov., from human dental plaque. Int J Syst Bacteriol. 1994 Apr;44(2):324-9. Pubmed: 8186098
  • Zhu J, Marchant RE: Dendritic saccharide surfactant polymers as antifouling interface materials to reduce platelet adhesion. Biomacromolecules. 2006 Apr;7(4):1036-41. Pubmed: 16602718
Synthesis Reference: Pedersen, Sven; Vang Hendriksen, Hanne. Method for production of maltose and/or enzymatically modified starch. PCT Int. Appl. (2001), 99 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17306
HMDB IDHMDB00163
Pubchem Compound ID439186
Kegg IDC00208
ChemSpider ID9166684
WikipediaMalt sugar
BioCyc IDMALTOSE
EcoCyc IDMALTOSE

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).