twitter

MetaCyc Compound Class: maltose

Synonyms: α-D-glucopyranose-(1→4)-D-glucopyranose, maltose

Superclasses: all carbohydrates a carbohydrate a glycan an oligosaccharide a disaccharide
all carbohydrates a carbohydrate a glycan an oligosaccharide a malto-oligosaccharide a linear malto-oligosaccharide

Summary:
Maltose is composed of two glucose molecules linked by an α 1,4-glycosidic linkage. Maltose is produced by the hydrolysis of starch and similar compounds, and can be hydrolyzed to glucose by the enzyme maltase.

maltose compound structure

maltose compound structure

Chemical Formula: C12H22O11

Instances:
α-maltose ,
β-maltose

Citations: [Stryer88]

Molecular Weight: 342.3 Daltons

Monoisotopic Molecular Weight: 342.11621154930003 Daltons

SMILES: C(C1(OC(C(C(C1O)O)O)OC2(C(OC(C(C2O)O)O)CO)))O

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

InChIKey: InChIKey=GUBGYTABKSRVRQ-PICCSMPSSA-N

Unification Links: CAS:69-79-4 , ChEBI:17306 , ChemSpider:6019

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -150.79538 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glycogen degradation I (bacterial) :
maltotetraose + D-glucopyranose ← maltotriose + maltose

starch degradation I :
a linear malto-oligosaccharide [(glucose)n] + H2O → maltose
maltose + H2O → β-D-glucopyranose + α-D-glucose

starch degradation II :
a linear malto-oligosaccharide [(glucose)n] + H2O → a linear malto-oligosaccharide [(glucose)n-2] + maltose

starch degradation V :
a maltodextrin(n+1) + α-D-glucose ← a maltodextrin(n) + maltose

sucrose biosynthesis II :
SHG-glucosyln+1 + β-D-glucopyranose ← SHG-glucosyln + maltose

Not in pathways:
maltose + H2O → β-D-glucopyranose + α-D-glucose
maltose + H2O → 2 glucose

Reactions known to produce the compound:

glycogen degradation I (bacterial) :
maltotriose + H2O → maltose + D-glucopyranose

starch degradation II :
an exposed unphosphorylated, unbranched malto-oligosaccharide tail on amylopectin[chloroplast stroma] + n H2O[chloroplast stroma]maltose[chloroplast stroma] + an exposed unphosphorylated, (α-1,6)-branched malto-oligosaccharide tail on amylopectin[chloroplast stroma]
an exposed unphosphorylated, unbranched malto-oligosaccharide tail on amylopectin[chloroplast stroma] + n H2O[chloroplast stroma] → amylopectin[chloroplast stroma] + maltose[chloroplast stroma]

starch degradation IV :
a maltodextrin + H2O → maltose + α-D-glucose

starch degradation V :
starch[extracellular space] + H2O[extracellular space] → a maltodextrin(n)[extracellular space] + maltose[extracellular space] + D-glucopyranose[extracellular space]

Not in pathways:
a 1,4-α-D-glucan + H2O → a 1,4-α-D-glucan + maltose
(1,6-α-D-glucosyl)(m+1) + H2O → (1,6-α-D-glucosyl)(m-1) + maltose
α-maltose 6'-phosphate + H2O → maltose + phosphate
starch + H2O → maltose + glucose

starch degradation I :
starch → a linear malto-oligosaccharide

starch degradation II :
an exposed unphosphorylated, (α-1,6)-branched malto-oligosaccharide tail on amylopectin[chloroplast stroma] + n H2O[chloroplast stroma] → amylopectin[chloroplast stroma] + n a linear malto-oligosaccharide[chloroplast stroma]

Not in pathways:
a long-linear glucan + n H2O → a linear malto-oligosaccharide

starch biosynthesis :
n a (1,6)-α-D-glucosyl-(1,4)-α-glucan highly branched[chloroplast stroma] + n H2O[chloroplast stroma] → n a malto-oligosaccharide[chloroplast stroma] + n (1,6)-α-D-glucosyl-(1,4)-α-glucan moderately branched[chloroplast stroma]

Not in pathways:
keratan sulfate + H2O → n an oligosaccharide
blood group substance B + H2O → n an oligosaccharide
blood group substance A + H2O → n an oligosaccharide
a sialyloligosaccharide + H2O → an oligosaccharide + N-acetylneuraminate
a 1,2-β-D-glucan + H2O → n an oligosaccharide
a fucoidan + H2O → fucose + a fucose sulfate + an oligosaccharide

Reactions known to both consume and produce the compound:

maltose degradation :
maltose + phosphate ↔ β-D-glucose 1-phosphate + β-D-glucopyranose

trehalose biosynthesis IV :
maltose ↔ α,α-trehalose

Not in pathways:
maltose + acetyl-CoA ↔ acetylmaltose + coenzyme A

In Reactions of unknown directionality:

Not in pathways:
maltohexaose + β-D-glucopyranose = maltopentaose + maltose
maltopentaose + D-glucopyranose = maltotetraose + maltose
2 α-D-glucopyranose 1-phosphate + H2O = maltose + 2 phosphate
maltose + H2O = 2 β-D-glucopyranose
maltohexaose + maltose = maltoheptaose + β-D-glucopyranose

Not in pathways:
a linear malto-oligosaccharide [(glucose)n] + phosphate = a linear malto-oligosaccharide [(glucose)n-1] + α-D-glucopyranose 1-phosphate

In Transport reactions:
maltose[chloroplast stroma]maltose[cytosol] ,
maltose[cco-cytosol-cco-chlor-str]maltose[cco-cytosol-cco-chlor-str] ,
maltose[extracellular space] + ATP + H2O → maltose[cytosol] + ADP + phosphate + H+ ,
maltose[extracellular space] + H+[extracellular space]maltose[cytosol] + H+[cytosol] ,
maltose[extracellular space]maltose[periplasmic space] ,
maltose[periplasmic space] + ATP + H2O → maltose[cytosol] + ADP + phosphate + H+ ,
maltose[periplasmic space]maltose[cytosol] ,
a [PTS enzyme I]-Nπ-phospho-L-histidine + maltose[out] → maltose 6'-phosphate[in] + a [PTS enzyme I]-L-histidine ,
an oligosaccharide[extracellular space] + ATP + H2O ↔ an oligosaccharide[cytosol] + ADP + phosphate

Enzymes inhibited by maltose, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: sucrose transporter [Sauer94] , sucrose transporter [Sauer94] , UDP-α-D-glucose:glucosyl-glycogenin α-D-glucosyltransferase [Cao93] , UDP-α-D-glucose:glycogenin α-D-glucosyltransferase [Cao93]

This compound has been characterized as an alternative substrate of the following enzymes: isoprimeverose α-xylosidase , kojibiose phosphorylase , D-glucose dehydrogenase , α-1,4-glucan lyase , maltodextrin glucosidase , sucrose 3-dehydrogenase , aldose sugar dehydrogenase

Credits:
Created 29-Sep-2012 by Caspi R , SRI International


References

Cao93: Cao Y, Mahrenholz AM, DePaoli-Roach AA, Roach PJ (1993). "Characterization of rabbit skeletal muscle glycogenin. Tyrosine 194 is essential for function." J Biol Chem 268(20);14687-93. PMID: 8325847

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Sauer94: Sauer N, Stolz J (1994). "SUC1 and SUC2: two sucrose transporters from Arabidopsis thaliana; expression and characterization in baker's yeast and identification of the histidine-tagged protein." Plant J 6(1);67-77. PMID: 7920705

Stryer88: Stryer L "Biochemistry." WH Freeman and Co., 3rd edition, New York, 1988.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Tue Jul 28, 2015, biocyc13.